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Spectroscopic Behavior and Photophysical Parameters of 2-(Acetoxymethyl)-6-(1,2,4-triazinylaminodihydroquinazolinyl)tetrahydropyran Derivative in Different Solid Hosts

Spectroscopic Behavior and Photophysical Parameters of... Optical and photophysical properties of 6-substituted-1,2,4-Triazine fluorescent derivative dye doped in silicate based sol– gel, homopolymer of methyl methacrylate (PMMA), and copolymer (MMA/diethylene glycol dimethacrylate) (DEGDMA) were investigated. The pores of different hosts and caging of the dye were found to effect on the parameters such as molar absorptivity, cross sections of singlet–singlet electronic absorption and emission spectra, excited state lifetime, quantum yield of fluorescence. The dipole moment of electronic transition, the length of attenuation and oscillator strength of electronic rd transition from So → S1 have been calculated. The dye was pumped with different powers using 3  harmonic Nd: YAG laser of 355 nm and pulse duration 8 ns, with repetition rate 10 Hz. Good photo stability for dye was attained. After 55,000 pumping pulses of (10 mJ/pulse), the photo-stabilities were decreased to 53%, 48%, and 45% of the initial ASE of dye in sol gel, PMMA, and Co-polymer respectively. The dye in sol–gel matrix showed improvement of photo stability compared with those in organic polymeric matrices. Keywords Optical property · Solid state laser dye · Photophysical parameters · Photostability · Silicate based sol–gel · Polymeric matrices Introduction 1,2,4-Triazine derivatives have been reported to possess a broad spectrum of biological activities including anti- 1,2,4-triazine is an important core system and many of inflammatory [2 ] antimicrobial [3, 4], anti-HIV [5], anti- their derivatives have gained considerable attention because cancer [6–8], anti haemostatic activity [9], antiviral [10], they are found in numerous natural and synthetic biologi- anti-malarial [11], anticonvulsant [8], neuro protective [12], cally as well as pharmacologically active compounds [1]. antifungal [13], anti-proliferation [14]. Some 1,2,4-triazine derivatives have also used as kinase inhibitors [15], and α-glucosidase inhibitors [16]. Also fused heterocyclic sys- tems that contain nitrogen were reported to exhibit fluores- * Mahmoud E. M. Sakr m.sakr@niles.edu.eg cent activity [17]. They are also widely applied as LEDs, lasers of semiconductors, probes, and fluorescent sensors. * Maram T. H. Abou Kana mabou202@niles.edu.eg In the development of organic LED (OLED) technologies trends are focused primarily on optimizing existing devices Laser Sciences and Interactions Department, National and developing new emission materials [18, 19]. In recent Institute of Laser-Enhanced Sciences (NILES), Cairo years, the synthesis of new high-performance dyes and the University, Giza, Egypt 2 implementation of new ways of incorporating the organic Chemistry Department, Faculty of Science, Cairo University, molecules into the solid matrix have resulted in significant Giza, Egypt 3 advances towards the development of practical tunable solid- Chemistry Department, Faculty of Science, Tanta University, state dye lasers, due to their high efficiency and they do not Tanta, Egypt 4 contain volatile and toxic solvents, they are non-flammable, Misr University for Science and Technology (MUST), nontoxic, compact in size and mechanically and thermally 6th of October City, Egypt Vol.:(0123456789) 1 3 1510 Journal of Fluorescence (2022) 32:1509–1516 more stable [20–23]. The sol–gel method is a method in Solid hosts as; silicate based sol–gel matrix and poly- which organic dye molecules are incorporated into an inor- mer (using methyl methacrylate MMA and diethylene glycol ganic silica host [24]. This shows some advantages, e.g. dimethacrylate DEGDMA as monomers) were prepared as compactness, better manageability and highly porous, trans- described in references [28] and [29, 30], respectively. parent in Uv–visible-near IR regions. Its reaction can be controlled easily by chemical methods. It allows introducing Spectral Measurements permanent organic groups to form inorganic–organic hybrid –5 materials [25] and the process takes place at low tempera- Dye samples of concentrations ranging from 2 × 10  M to –4 ture [26]. In this respect we recently reported the synthesis 3 × 10  M were doped in transparent sol–gel, PMMA and of 6-Substituted-1, 2, 4-Triazine mono glucosyl fluorescent (MMA / DEGDMA) Co-polymer. The electronic absorp- derivative dye and investigated their optical, photo physi- tion properties of the dye samples in different solid hosts cal and solvatochromic properties [27]. In continuation were studies using a Camspec M501 UV–Vis spectropho- of this work, the present study discuss the spectral behav- tometer. The emission spectra were monitored, depend upon ior and photophysical parameters of 6-substituted-1,2,4- exciting wavelength which represent maximum absorption, triazine mono glucosyl fluorescent derivative dye doped using JASCO-spectrofluorometer (model: PF-6300). Laser in various solid hosts matrices including sol–gel, PMMA induced fluorescence of dye samples as function of different rd and Co-PMMA. Although a lot of dyes are commercially input pumping energies were carried out by 3 harmonic available for laser systems, but the previous ones have a Nd: YAG laser using homemade setup as previously reported pointing of advantages such as larger Stokes shift magnitude [31]. The photostability of the dye was also determined [32]. (Δλ > 100 nm) which can minimize cross-talk between the The input energy was kept constant at (10 mJ) by pumping excitation source and the fluorescent emission [28]. with 355 nm of 3rd harmonic Nd: YAG laser. PhotoPhysical Parameters Calculations Experimental Depending upon these absorption and emission spectra, important and significant photophysical parameters could Materials be determined according to their standard equations as pre- viously reported such as: the oscillator strength [33], the Active triazine derivative as chromophore was recently pre- attenuation length Λ() [34], the dipole moment transition pared and reported in described form by our lab’team [27] μ [34], the rate of radiative decay constant (kr) [35], the absorption cross-section σ [36], the quantum yield (ϕ ) of a a f compound relative to a standard probe [37, 38], fluorescence lifetimes (τ ) [39], the rate constant of intersystem crossing (kisc) which related to the quantum yield ϕ for (ϕf ≈1) by the relationship (1) [35]: k = 1 −  ∕ (1) isc f f Also, the emission cross-section σ was calculated accord- ing to ref. [40]. Results and Discussion Photphysical Properties in Different Hosts The UV–visible absorption and fluorescence spectra of the dye in sol–gel, homo-polymer PMMA and (MMA / DEG- DMA) copolymer matrices as solid hosts are shown in Figs. 1 and 2. There is a minimum overlap between the dye absorption and emission spectra in the three solid matrices. 1 3 Journal of Fluorescence (2022) 32:1509–1516 1511 Fig. 1 Normalized absorption spectra and the emission spectra –5 of dye of 7 × 10  M with excited wavelength 385 nm in sol–gel (the inset figure shows the dye emission intensity as function of different concentra- tions) This is important as far as reabsorption of emitted photons to due molecular aggregations of dye molecules which is concerned. Figure 1 shows that the absorption maximum absorbed the emitted photon. peak of dye was 385 nm and the emission maximum peak Figure 2A, B shows that the absorption maximum peaks was at 520 nm in sol–gel, respectively. Inset Fig. 1 shows were at 365 and 370 nm in PMMA and (MMA/DEGDMA), that the emission of the dye of different concentrations in respectively. It also shows that the emission maximum sol–gel at excitation wavelengths 385 nm. The optimum dye peaks were at 445 nm and 450 nm for the dye in PMMA –5 concentration was 7 × 10  M in sol–gel. The dye fluores- and (MMA/DEGDMA), respectively. Inset Fig. 2A, B shows –5 cence peak intensity increased till 7 × 10  M then decreased that the emission of the dye at different concentrations in with increasing concentrations which might be attributed in PMMA and (MMA/DEGDMA) at excitation wavelength –5 Fig. 2 (A, B) The absorption and emission spectra of 5 × 10  M dye in A) PMMA and B) (MMA/DEGDMA) Co-polymer with excited wave- length 365 nm and 370 nm, respectively. (The inset figures focus on the dye emission intensity as function of different concentrations) 1 3 1512 Journal of Fluorescence (2022) 32:1509–1516 365 nm, and 370 nm respectively. The dye emission spectra in which the polymer matrices interact with the excited with different concentrations doped in PMMA and (MMA/ state dye molecules. This leads to shortening of τ values DEGDMA) Co-polymer was shown in inset Fig. 2A, B. The in polymer matrices compared with sol–gel. The oscilla- –5 dye fluorescence peak intensity increased till 5 × 10  M in tor strength value in sol–gel matrix is higher than those in –4 case of PMMA and 1 × 10 in case of (MMA/DEGDMA) polymer matrices. Hence, the effective number of electrons Co-polymer then it decreased with increasing concentra- transferred from the ground to excited states in sol–gel is tions which might be attributed to molecular aggregations higher than that in polymer matrices. Fluorescence quantum of dye molecules. Also, the optimum dye concentration was yield (ϕ ) values are lower in polymer and in copolymer –5 –4 5 × 10   M and 1 × 10   M in PMMA and (MMA/DEG- matrices compared with those in sol–gel, indicating more DMA) Co-polymer, respectively. interaction between dye molecules and polymer matrices. From the Figs. 1 and 2 show that the absorption maxi- The carbonyl group in chromophore polymer matrices pos- mum peaks were 385 nm, 365 nm and 370 nm in sol gel, sesses (n, π*) electronic states that are characterized by low PMMA and (MMA/DEGDMA), respectively, and the emis- singlet—triplet splitting energies (ΔES,T) leading to triplet sion maximum peaks were 520 nm, 445 nm and 450 nm in state population from singlet excited state, with subsequent sol gel, PMMA and (MMA/DEGDMA), respectively. We fluorescence quenching [34]. It is known that the (T1 → Tn) found that the nature of polymer either homo-polymer or transition is a spin- allowed one that can quench fluorescence copolymer has no effect on the absorption intensity of the by photon re-absorption. The lower energy level of (n, π*) dye, but it has clear effect of its absorption wavelength. states also allows for exciton trapping [34] adding to factors This effect may be attributed to the nature of interaction causing fluorescence quenching. Further confirmation of the between dye and DEGDMA which contains different active role of polymer matrices in fluorescence quenching comes groups. Comparing the dye fluorescence peak wavelengths from the higher intersystem crossing rate constants (k ) isc and intensities in different solid matrices showed that, the values in polymer matrices compared with sol–gel glass. fluorescence emission wavelengths are higher red shifted in sol–gel compared to polymer matrices. This behavior indi- Laser‑induced Fuorescence of 6‑substituted‑1,2, cates a more relaxed excited state due to dye host interaction 4‑triazines Mono Glucosyl Derivative within excited state lifetime. Some important photo-physical parameters of the dye were calculated and summarized in The spontaneous fluorescence intensities and wavelengths Table  1, which demonstrate their potential for use  in of the 6-substituted-1,2,4-triazines mono glucosyl deriva- advanced optical applications. However, the absorption tive dye in sol gel, PMMA and (MMA/DEGDMA) copoly- rd cross-section (σa) is the ability of the molecule to absorb a mer were varied after pumping with 3 harmonic Nd:YAG photon of a certain polarization and wavelength. Emission (λ = 355 nm). Emission intensity of ASE of the dye with con- –5 –4 cross-section (σe) measures the probability of the excited ion centrations range from 2 × 10  M to 3 × 10  M in PMMA, in a given cross sectional area to emit a photon. The attenu- Co-PMMA (MMA/DEGDMA), and sol–gel with excited rd ation length (L) (called absorption length) is the distance wavelength 355 nm by 3r d  harmonic Nd: YAG pulsed laser into a material when the probability has dropped to1/e that at pumping power 5 mJ. We found that the concentration –4 a particle has not been absorbed. 3 × 10 after pumping the different concentration by 5 mJ It is noticed from photophysical parameters of dye in dif- is the highest emission intensity of the dye in PMMA, Co- ferent solid hosts that excited state lifetime (τ ) values in PMMA (MMA/DEGDMA) and sol–gel then pumping these –4 PMMA and in copolymer matrices are lower than those in concentration 3 × 10 with excitation wavelength 355 nm sol–gel matrix. This indicates a dynamic quenching process by 3rd harmonic Nd:YAG pulsed laser with different Table 1 Photophysical parameters of the dye in different hosts; (ε) moment transition, (Ef) energy yield of fluorescence, (Kr) the radia- molecular extinction coefficient; σa and σe: cross section of absorp- tive decay rate, (Kisc) the rate of intersystem crossing, (f) oscillator tion and emission; (Λ) the attenuation length, (τf) fluorescence strength, φf fluorescence quantum yield, in different hosts life time, (τo) calculated fluorescence life time, μ12(D) the dipole Sample /matrix ε σ σ Λ (cm) τ τ μ E K K F φ a e f 0 12 f r isc f −1 –16 2 –17 2 9) 9 L.M . (10 ) Cm (10 ) Cm (ns) (1/k ) (D) (10 (10 ) −1 −1 −1 Cm (ns) s s (10 ) Solgel 1.5 0.6 2,2 0.2 0.6 0.9 3.53 0.31 1.1 0.9 1.74 0.7 PMMA 3.5 1.4 2.6 0.1 0.2 0.4 3.35 0.28 2.8 1.8 1.33 0.6 (MMA/DEGDMA) 3.5 1.3 2.4 0.1 0.2 0.4 2.96 0.23 2.6 1.6 1.02 0.5 1 3 Journal of Fluorescence (2022) 32:1509–1516 1513 input pumping powers 5 mJ, 10 mJ, 20 mJ as showed in dye in the excited state with other species such as impurities, Fig. 3A−C. other dye molecules and singlet oxygen. Through the process rd By pumping using 355 nm 3rd harmonic Nd: YAG pulsed of doping dyes into a solid medium, the photochemical path- laser with λ = 355 nm excitation wavelength at different pow - ways including bimolecular reactions can be suppressed by ex ers intensity 5 mJ, 10 mJ, and 20 mJ. The emission intensity of caging or trapping the dye within a solid host [41]. ASE peak wavelength of the dye in sol gel matrix (λ = 550 nm) The improved photostability of the dyes within solid showed a large red shift from that of the dye in PMMA hosts has been attributed for caging and molecules immobi- (λ = 475 nm) and (MMA/DEGDMA) matrix (λ = 480  nm) lizing of the dye, minimizing thereby excited-state interac- f f as in Fig. 3. Figure 3 showed the emission intensity of the tion with other species including molecular oxygen. So, the dye in solid hosts at different input power at 5, 10 and 20 mJ. dye photodegradation in a solid host depends on the dye’s The increasing of the peak intensity of ASE of the dye may be molecule nature, the host composition and structure, the host attributed to the increasing of the number of excited molecules impurities as well as presence of molecular oxygen. Another (increase the population of S1 state) which yields more emit- possible factor that may explains the reduced rate of degra- ted photons. These changes in wavelengths may be due to the dation in the rigid matrices may be that the dyes molecules interaction of the structure of the two different dyes molecules are more tightly confined within the pores of the matrix, with different solid matrices as shown in Fig.  3. limiting rotational and translational freedom. A mobile The photostability, as an important photochemical param- molecule, as in solution, will be more likely to encounter eter, was studied by the evaluation of the output fluorescence an oxygen molecule and undergo degradation. Less free- as a function of number of pulses in the same position of the dom, as defined by the restrictive pores of the matrix, may samples as outlined in Fig. 4. This study was carried out for make the dye molecules less likely to interact with molecular the samples of the dyes which the repetition rate of 355 nm oxygen leading to photodegradation or molecular oxygen Nd: YAG laser with 8 ns pulse duration was kept at (10 Hz) fluorescence quenching [41]. The micro-viscosity environ- and the energy was kept constant at (10 mJ/pulse). The out- ment around dye molecules in the solid matrix affects their put energy gradually decreased due to the photodegradation photodegradation. The net photo deterioration would be progressive and thermo-degradation of the dye’s molecules. slow if the irradiated molecules were swiftly replaced by This decreasing occurred at a faster rate for the dyes in poly- fresh molecules. As a result, photo degradation in sol–gel mer than in sol gel, and the peak ASE dropped to 53%, 48% samples is negligible, with the longest half-life values. On and 45% of the initial ASE of the dye in sol–gel, PMMA and the other hand, photo degradation occurs at a faster pace in (MMA/DEGDMA) Co-PMMA, respectively, by pumping with the copolymer samples. This is because dye molecules in rd 355 nm 3 harmonic Nd: YAG laser at 10 mJ with repetition polymer samples are surrounded only by polymer matrix rate of 10 Hz after 55,000 pulses. Since the mechanism of with very little solvent around them, whereas dye mol- photodegradation occurs by the interaction molecules of the ecules in sol–gel matrix are rapidly replenished because Fig. 3 (A, B): A) Emission intensities at input pumping power 5 mJ, and B) The output powers at different input pumping powers 5 mJ, 10 mJ, 20 mJ rd of the dye in PMMA, Co-PMMA(MMA/DEGDMA), and sol–gel with excited wavelength 355 nm by 3rd harmonic Nd:YAG pulsed laser 1 3 1514 Journal of Fluorescence (2022) 32:1509–1516 Fig. 4 Normalized output energy of the dye as a func- tion of the number of pump pulses using pumping power of 355 nm 3rd harmonic Nd: YAG laser at 10 mJ investigation, supervision, writing original draft. Ahmed H. M. sol–gel samples contain ethylene glycol, which may aid in Elwahy: Conceptualization, supervision, investigation, review, edit- the mobility of the embedded dye molecules, resulting in ing. Mohamed S. Abdelwahed: Synthesis, resources. Samy A. El-Daly: minimal photodegradation and the longest half-life values. Review, supervision. El-Zeiny M. Ebeid: Review, supervision. Funding Open access funding provided by The Science, Technology & Conclusion Innovation Funding Authority (STDF) in cooperation with The Egyp- tian Knowledge Bank (EKB). The optical absorption and emission properties of  2- Data Availability Data generated or analyzed during this study are (acetoxymethyl)-6-(1,2,4-triazinylaminodihydroquinazolinyl) included in this published article. tetrahydropyran dye have been studied in different solid hosts such as sol–gel, PMMA and DEGDMA copolymer. Their Declarations respective spectroscopic and photophysical parameters meet the best requirements for a good laser dye such as high molar Ethical Approval This article does not contain any studies with human absorption coefficients at the wavelength of the pump laser, or animal subjects. broad spectral region of fluorescence and high fluorescence Consent to Participate Not applicable. quantum yield, short fluorescence decay time, large Stokes' shift, little overlap of the fluorescence and triplet absorption Consent for Publication Not applicable. spectral regions, photochemical stability. Pumping the sam- rd ples using 3 harmonic Nd: YAG laser (λ = 355 nm) showed ex Conflicts of Interest The authors declare that they have no conflict of differ ent emission wavelength of ASE peak. It was nearly in interest. sol gel matrix (λ = 550 nm), in PMMA (λ = 475  nm) and f f (MMA/DEGDMA) copolymer (λ = 480 nm). The nature of Open Access This article is licensed under a Creative Commons Attri- bution 4.0 International License, which permits use, sharing, adapta- solid host has significant effect on spectroscopic properties of tion, distribution and reproduction in any medium or format, as long dye. The new dye exhibited good photostability. It decreased as you give appropriate credit to the original author(s) and the source, to 53%, 48% and 45% of the initial ASE of the dye in sol–gel, provide a link to the Creative Commons licence, and indicate if changes PMMA and DEGDMA copolymer, respectively, after pump- were made. The images or other third party material in this article are rd included in the article's Creative Commons licence, unless indicated ing with 355 nm 3 harmonic Nd: YAG laser of 8 ns pulse otherwise in a credit line to the material. If material is not included in duration, with a repetition rate (10 Hz). 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Spectroscopic Behavior and Photophysical Parameters of 2-(Acetoxymethyl)-6-(1,2,4-triazinylaminodihydroquinazolinyl)tetrahydropyran Derivative in Different Solid Hosts

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Abstract

Optical and photophysical properties of 6-substituted-1,2,4-Triazine fluorescent derivative dye doped in silicate based sol– gel, homopolymer of methyl methacrylate (PMMA), and copolymer (MMA/diethylene glycol dimethacrylate) (DEGDMA) were investigated. The pores of different hosts and caging of the dye were found to effect on the parameters such as molar absorptivity, cross sections of singlet–singlet electronic absorption and emission spectra, excited state lifetime, quantum yield of fluorescence. The dipole moment of electronic transition, the length of attenuation and oscillator strength of electronic rd transition from So → S1 have been calculated. The dye was pumped with different powers using 3  harmonic Nd: YAG laser of 355 nm and pulse duration 8 ns, with repetition rate 10 Hz. Good photo stability for dye was attained. After 55,000 pumping pulses of (10 mJ/pulse), the photo-stabilities were decreased to 53%, 48%, and 45% of the initial ASE of dye in sol gel, PMMA, and Co-polymer respectively. The dye in sol–gel matrix showed improvement of photo stability compared with those in organic polymeric matrices. Keywords Optical property · Solid state laser dye · Photophysical parameters · Photostability · Silicate based sol–gel · Polymeric matrices Introduction 1,2,4-Triazine derivatives have been reported to possess a broad spectrum of biological activities including anti- 1,2,4-triazine is an important core system and many of inflammatory [2 ] antimicrobial [3, 4], anti-HIV [5], anti- their derivatives have gained considerable attention because cancer [6–8], anti haemostatic activity [9], antiviral [10], they are found in numerous natural and synthetic biologi- anti-malarial [11], anticonvulsant [8], neuro protective [12], cally as well as pharmacologically active compounds [1]. antifungal [13], anti-proliferation [14]. Some 1,2,4-triazine derivatives have also used as kinase inhibitors [15], and α-glucosidase inhibitors [16]. Also fused heterocyclic sys- tems that contain nitrogen were reported to exhibit fluores- * Mahmoud E. M. Sakr m.sakr@niles.edu.eg cent activity [17]. They are also widely applied as LEDs, lasers of semiconductors, probes, and fluorescent sensors. * Maram T. H. Abou Kana mabou202@niles.edu.eg In the development of organic LED (OLED) technologies trends are focused primarily on optimizing existing devices Laser Sciences and Interactions Department, National and developing new emission materials [18, 19]. In recent Institute of Laser-Enhanced Sciences (NILES), Cairo years, the synthesis of new high-performance dyes and the University, Giza, Egypt 2 implementation of new ways of incorporating the organic Chemistry Department, Faculty of Science, Cairo University, molecules into the solid matrix have resulted in significant Giza, Egypt 3 advances towards the development of practical tunable solid- Chemistry Department, Faculty of Science, Tanta University, state dye lasers, due to their high efficiency and they do not Tanta, Egypt 4 contain volatile and toxic solvents, they are non-flammable, Misr University for Science and Technology (MUST), nontoxic, compact in size and mechanically and thermally 6th of October City, Egypt Vol.:(0123456789) 1 3 1510 Journal of Fluorescence (2022) 32:1509–1516 more stable [20–23]. The sol–gel method is a method in Solid hosts as; silicate based sol–gel matrix and poly- which organic dye molecules are incorporated into an inor- mer (using methyl methacrylate MMA and diethylene glycol ganic silica host [24]. This shows some advantages, e.g. dimethacrylate DEGDMA as monomers) were prepared as compactness, better manageability and highly porous, trans- described in references [28] and [29, 30], respectively. parent in Uv–visible-near IR regions. Its reaction can be controlled easily by chemical methods. It allows introducing Spectral Measurements permanent organic groups to form inorganic–organic hybrid –5 materials [25] and the process takes place at low tempera- Dye samples of concentrations ranging from 2 × 10  M to –4 ture [26]. In this respect we recently reported the synthesis 3 × 10  M were doped in transparent sol–gel, PMMA and of 6-Substituted-1, 2, 4-Triazine mono glucosyl fluorescent (MMA / DEGDMA) Co-polymer. The electronic absorp- derivative dye and investigated their optical, photo physi- tion properties of the dye samples in different solid hosts cal and solvatochromic properties [27]. In continuation were studies using a Camspec M501 UV–Vis spectropho- of this work, the present study discuss the spectral behav- tometer. The emission spectra were monitored, depend upon ior and photophysical parameters of 6-substituted-1,2,4- exciting wavelength which represent maximum absorption, triazine mono glucosyl fluorescent derivative dye doped using JASCO-spectrofluorometer (model: PF-6300). Laser in various solid hosts matrices including sol–gel, PMMA induced fluorescence of dye samples as function of different rd and Co-PMMA. Although a lot of dyes are commercially input pumping energies were carried out by 3 harmonic available for laser systems, but the previous ones have a Nd: YAG laser using homemade setup as previously reported pointing of advantages such as larger Stokes shift magnitude [31]. The photostability of the dye was also determined [32]. (Δλ > 100 nm) which can minimize cross-talk between the The input energy was kept constant at (10 mJ) by pumping excitation source and the fluorescent emission [28]. with 355 nm of 3rd harmonic Nd: YAG laser. PhotoPhysical Parameters Calculations Experimental Depending upon these absorption and emission spectra, important and significant photophysical parameters could Materials be determined according to their standard equations as pre- viously reported such as: the oscillator strength [33], the Active triazine derivative as chromophore was recently pre- attenuation length Λ() [34], the dipole moment transition pared and reported in described form by our lab’team [27] μ [34], the rate of radiative decay constant (kr) [35], the absorption cross-section σ [36], the quantum yield (ϕ ) of a a f compound relative to a standard probe [37, 38], fluorescence lifetimes (τ ) [39], the rate constant of intersystem crossing (kisc) which related to the quantum yield ϕ for (ϕf ≈1) by the relationship (1) [35]: k = 1 −  ∕ (1) isc f f Also, the emission cross-section σ was calculated accord- ing to ref. [40]. Results and Discussion Photphysical Properties in Different Hosts The UV–visible absorption and fluorescence spectra of the dye in sol–gel, homo-polymer PMMA and (MMA / DEG- DMA) copolymer matrices as solid hosts are shown in Figs. 1 and 2. There is a minimum overlap between the dye absorption and emission spectra in the three solid matrices. 1 3 Journal of Fluorescence (2022) 32:1509–1516 1511 Fig. 1 Normalized absorption spectra and the emission spectra –5 of dye of 7 × 10  M with excited wavelength 385 nm in sol–gel (the inset figure shows the dye emission intensity as function of different concentra- tions) This is important as far as reabsorption of emitted photons to due molecular aggregations of dye molecules which is concerned. Figure 1 shows that the absorption maximum absorbed the emitted photon. peak of dye was 385 nm and the emission maximum peak Figure 2A, B shows that the absorption maximum peaks was at 520 nm in sol–gel, respectively. Inset Fig. 1 shows were at 365 and 370 nm in PMMA and (MMA/DEGDMA), that the emission of the dye of different concentrations in respectively. It also shows that the emission maximum sol–gel at excitation wavelengths 385 nm. The optimum dye peaks were at 445 nm and 450 nm for the dye in PMMA –5 concentration was 7 × 10  M in sol–gel. The dye fluores- and (MMA/DEGDMA), respectively. Inset Fig. 2A, B shows –5 cence peak intensity increased till 7 × 10  M then decreased that the emission of the dye at different concentrations in with increasing concentrations which might be attributed in PMMA and (MMA/DEGDMA) at excitation wavelength –5 Fig. 2 (A, B) The absorption and emission spectra of 5 × 10  M dye in A) PMMA and B) (MMA/DEGDMA) Co-polymer with excited wave- length 365 nm and 370 nm, respectively. (The inset figures focus on the dye emission intensity as function of different concentrations) 1 3 1512 Journal of Fluorescence (2022) 32:1509–1516 365 nm, and 370 nm respectively. The dye emission spectra in which the polymer matrices interact with the excited with different concentrations doped in PMMA and (MMA/ state dye molecules. This leads to shortening of τ values DEGDMA) Co-polymer was shown in inset Fig. 2A, B. The in polymer matrices compared with sol–gel. The oscilla- –5 dye fluorescence peak intensity increased till 5 × 10  M in tor strength value in sol–gel matrix is higher than those in –4 case of PMMA and 1 × 10 in case of (MMA/DEGDMA) polymer matrices. Hence, the effective number of electrons Co-polymer then it decreased with increasing concentra- transferred from the ground to excited states in sol–gel is tions which might be attributed to molecular aggregations higher than that in polymer matrices. Fluorescence quantum of dye molecules. Also, the optimum dye concentration was yield (ϕ ) values are lower in polymer and in copolymer –5 –4 5 × 10   M and 1 × 10   M in PMMA and (MMA/DEG- matrices compared with those in sol–gel, indicating more DMA) Co-polymer, respectively. interaction between dye molecules and polymer matrices. From the Figs. 1 and 2 show that the absorption maxi- The carbonyl group in chromophore polymer matrices pos- mum peaks were 385 nm, 365 nm and 370 nm in sol gel, sesses (n, π*) electronic states that are characterized by low PMMA and (MMA/DEGDMA), respectively, and the emis- singlet—triplet splitting energies (ΔES,T) leading to triplet sion maximum peaks were 520 nm, 445 nm and 450 nm in state population from singlet excited state, with subsequent sol gel, PMMA and (MMA/DEGDMA), respectively. We fluorescence quenching [34]. It is known that the (T1 → Tn) found that the nature of polymer either homo-polymer or transition is a spin- allowed one that can quench fluorescence copolymer has no effect on the absorption intensity of the by photon re-absorption. The lower energy level of (n, π*) dye, but it has clear effect of its absorption wavelength. states also allows for exciton trapping [34] adding to factors This effect may be attributed to the nature of interaction causing fluorescence quenching. Further confirmation of the between dye and DEGDMA which contains different active role of polymer matrices in fluorescence quenching comes groups. Comparing the dye fluorescence peak wavelengths from the higher intersystem crossing rate constants (k ) isc and intensities in different solid matrices showed that, the values in polymer matrices compared with sol–gel glass. fluorescence emission wavelengths are higher red shifted in sol–gel compared to polymer matrices. This behavior indi- Laser‑induced Fuorescence of 6‑substituted‑1,2, cates a more relaxed excited state due to dye host interaction 4‑triazines Mono Glucosyl Derivative within excited state lifetime. Some important photo-physical parameters of the dye were calculated and summarized in The spontaneous fluorescence intensities and wavelengths Table  1, which demonstrate their potential for use  in of the 6-substituted-1,2,4-triazines mono glucosyl deriva- advanced optical applications. However, the absorption tive dye in sol gel, PMMA and (MMA/DEGDMA) copoly- rd cross-section (σa) is the ability of the molecule to absorb a mer were varied after pumping with 3 harmonic Nd:YAG photon of a certain polarization and wavelength. Emission (λ = 355 nm). Emission intensity of ASE of the dye with con- –5 –4 cross-section (σe) measures the probability of the excited ion centrations range from 2 × 10  M to 3 × 10  M in PMMA, in a given cross sectional area to emit a photon. The attenu- Co-PMMA (MMA/DEGDMA), and sol–gel with excited rd ation length (L) (called absorption length) is the distance wavelength 355 nm by 3r d  harmonic Nd: YAG pulsed laser into a material when the probability has dropped to1/e that at pumping power 5 mJ. We found that the concentration –4 a particle has not been absorbed. 3 × 10 after pumping the different concentration by 5 mJ It is noticed from photophysical parameters of dye in dif- is the highest emission intensity of the dye in PMMA, Co- ferent solid hosts that excited state lifetime (τ ) values in PMMA (MMA/DEGDMA) and sol–gel then pumping these –4 PMMA and in copolymer matrices are lower than those in concentration 3 × 10 with excitation wavelength 355 nm sol–gel matrix. This indicates a dynamic quenching process by 3rd harmonic Nd:YAG pulsed laser with different Table 1 Photophysical parameters of the dye in different hosts; (ε) moment transition, (Ef) energy yield of fluorescence, (Kr) the radia- molecular extinction coefficient; σa and σe: cross section of absorp- tive decay rate, (Kisc) the rate of intersystem crossing, (f) oscillator tion and emission; (Λ) the attenuation length, (τf) fluorescence strength, φf fluorescence quantum yield, in different hosts life time, (τo) calculated fluorescence life time, μ12(D) the dipole Sample /matrix ε σ σ Λ (cm) τ τ μ E K K F φ a e f 0 12 f r isc f −1 –16 2 –17 2 9) 9 L.M . (10 ) Cm (10 ) Cm (ns) (1/k ) (D) (10 (10 ) −1 −1 −1 Cm (ns) s s (10 ) Solgel 1.5 0.6 2,2 0.2 0.6 0.9 3.53 0.31 1.1 0.9 1.74 0.7 PMMA 3.5 1.4 2.6 0.1 0.2 0.4 3.35 0.28 2.8 1.8 1.33 0.6 (MMA/DEGDMA) 3.5 1.3 2.4 0.1 0.2 0.4 2.96 0.23 2.6 1.6 1.02 0.5 1 3 Journal of Fluorescence (2022) 32:1509–1516 1513 input pumping powers 5 mJ, 10 mJ, 20 mJ as showed in dye in the excited state with other species such as impurities, Fig. 3A−C. other dye molecules and singlet oxygen. Through the process rd By pumping using 355 nm 3rd harmonic Nd: YAG pulsed of doping dyes into a solid medium, the photochemical path- laser with λ = 355 nm excitation wavelength at different pow - ways including bimolecular reactions can be suppressed by ex ers intensity 5 mJ, 10 mJ, and 20 mJ. The emission intensity of caging or trapping the dye within a solid host [41]. ASE peak wavelength of the dye in sol gel matrix (λ = 550 nm) The improved photostability of the dyes within solid showed a large red shift from that of the dye in PMMA hosts has been attributed for caging and molecules immobi- (λ = 475 nm) and (MMA/DEGDMA) matrix (λ = 480  nm) lizing of the dye, minimizing thereby excited-state interac- f f as in Fig. 3. Figure 3 showed the emission intensity of the tion with other species including molecular oxygen. So, the dye in solid hosts at different input power at 5, 10 and 20 mJ. dye photodegradation in a solid host depends on the dye’s The increasing of the peak intensity of ASE of the dye may be molecule nature, the host composition and structure, the host attributed to the increasing of the number of excited molecules impurities as well as presence of molecular oxygen. Another (increase the population of S1 state) which yields more emit- possible factor that may explains the reduced rate of degra- ted photons. These changes in wavelengths may be due to the dation in the rigid matrices may be that the dyes molecules interaction of the structure of the two different dyes molecules are more tightly confined within the pores of the matrix, with different solid matrices as shown in Fig.  3. limiting rotational and translational freedom. A mobile The photostability, as an important photochemical param- molecule, as in solution, will be more likely to encounter eter, was studied by the evaluation of the output fluorescence an oxygen molecule and undergo degradation. Less free- as a function of number of pulses in the same position of the dom, as defined by the restrictive pores of the matrix, may samples as outlined in Fig. 4. This study was carried out for make the dye molecules less likely to interact with molecular the samples of the dyes which the repetition rate of 355 nm oxygen leading to photodegradation or molecular oxygen Nd: YAG laser with 8 ns pulse duration was kept at (10 Hz) fluorescence quenching [41]. The micro-viscosity environ- and the energy was kept constant at (10 mJ/pulse). The out- ment around dye molecules in the solid matrix affects their put energy gradually decreased due to the photodegradation photodegradation. The net photo deterioration would be progressive and thermo-degradation of the dye’s molecules. slow if the irradiated molecules were swiftly replaced by This decreasing occurred at a faster rate for the dyes in poly- fresh molecules. As a result, photo degradation in sol–gel mer than in sol gel, and the peak ASE dropped to 53%, 48% samples is negligible, with the longest half-life values. On and 45% of the initial ASE of the dye in sol–gel, PMMA and the other hand, photo degradation occurs at a faster pace in (MMA/DEGDMA) Co-PMMA, respectively, by pumping with the copolymer samples. This is because dye molecules in rd 355 nm 3 harmonic Nd: YAG laser at 10 mJ with repetition polymer samples are surrounded only by polymer matrix rate of 10 Hz after 55,000 pulses. Since the mechanism of with very little solvent around them, whereas dye mol- photodegradation occurs by the interaction molecules of the ecules in sol–gel matrix are rapidly replenished because Fig. 3 (A, B): A) Emission intensities at input pumping power 5 mJ, and B) The output powers at different input pumping powers 5 mJ, 10 mJ, 20 mJ rd of the dye in PMMA, Co-PMMA(MMA/DEGDMA), and sol–gel with excited wavelength 355 nm by 3rd harmonic Nd:YAG pulsed laser 1 3 1514 Journal of Fluorescence (2022) 32:1509–1516 Fig. 4 Normalized output energy of the dye as a func- tion of the number of pump pulses using pumping power of 355 nm 3rd harmonic Nd: YAG laser at 10 mJ investigation, supervision, writing original draft. Ahmed H. M. sol–gel samples contain ethylene glycol, which may aid in Elwahy: Conceptualization, supervision, investigation, review, edit- the mobility of the embedded dye molecules, resulting in ing. Mohamed S. Abdelwahed: Synthesis, resources. Samy A. El-Daly: minimal photodegradation and the longest half-life values. Review, supervision. El-Zeiny M. Ebeid: Review, supervision. Funding Open access funding provided by The Science, Technology & Conclusion Innovation Funding Authority (STDF) in cooperation with The Egyp- tian Knowledge Bank (EKB). The optical absorption and emission properties of  2- Data Availability Data generated or analyzed during this study are (acetoxymethyl)-6-(1,2,4-triazinylaminodihydroquinazolinyl) included in this published article. tetrahydropyran dye have been studied in different solid hosts such as sol–gel, PMMA and DEGDMA copolymer. Their Declarations respective spectroscopic and photophysical parameters meet the best requirements for a good laser dye such as high molar Ethical Approval This article does not contain any studies with human absorption coefficients at the wavelength of the pump laser, or animal subjects. broad spectral region of fluorescence and high fluorescence Consent to Participate Not applicable. quantum yield, short fluorescence decay time, large Stokes' shift, little overlap of the fluorescence and triplet absorption Consent for Publication Not applicable. spectral regions, photochemical stability. Pumping the sam- rd ples using 3 harmonic Nd: YAG laser (λ = 355 nm) showed ex Conflicts of Interest The authors declare that they have no conflict of differ ent emission wavelength of ASE peak. It was nearly in interest. sol gel matrix (λ = 550 nm), in PMMA (λ = 475  nm) and f f (MMA/DEGDMA) copolymer (λ = 480 nm). The nature of Open Access This article is licensed under a Creative Commons Attri- bution 4.0 International License, which permits use, sharing, adapta- solid host has significant effect on spectroscopic properties of tion, distribution and reproduction in any medium or format, as long dye. The new dye exhibited good photostability. It decreased as you give appropriate credit to the original author(s) and the source, to 53%, 48% and 45% of the initial ASE of the dye in sol–gel, provide a link to the Creative Commons licence, and indicate if changes PMMA and DEGDMA copolymer, respectively, after pump- were made. The images or other third party material in this article are rd included in the article's Creative Commons licence, unless indicated ing with 355 nm 3 harmonic Nd: YAG laser of 8 ns pulse otherwise in a credit line to the material. If material is not included in duration, with a repetition rate (10 Hz). 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Journal

Journal of Fluorescence – Springer Journals

Published: Jul 1, 2022

Keywords: Optical property; Solid state laser dye; Photophysical parameters; Photostability; Silicate based sol–gel; Polymeric matrices

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