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A. Coskun, M. Yilmaz, E. Akkaya (2007)
Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II).Organic letters, 9 4
P. ChinnaAyyaSwamy, Ragam Priyanka, S. Mukherjee, P. Thilagar (2015)
Panchromatic Borane–aza‐BODIPY Conjugate: Synthesis, Intriguing Optical Properties, and Selective Fluorescent Sensing of Fluoride AnionsEuropean Journal of Inorganic Chemistry, 2015
Yayang Wu, Chi-An Cheng, Lijuan Jiao, Changjiang Yu, Sufan Wang, Yun Wei, Xiaolong Mu, Erhong Hao (2014)
β-Thiophene-fused BF2-azadipyrromethenes as near-infrared dyes.Organic letters, 16 3
Yuan Ge, D. O’Shea (2016)
Azadipyrromethenes: from traditional dye chemistry to leading edge applications.Chemical Society reviews, 45 14
P. Bujak, I. Kulszewicz-Bajer, M. Zagórska, V. Maurel, I. Wielgus, A. Pron (2013)
Polymers for electronics and spintronics.Chemical Society reviews, 42 23
Tian‐yi Li, T. Meyer, R. Meerheim, M. Höppner, C. Körner, K. Vandewal, Olaf Zeika, K. Leo (2017)
Aza-BODIPY dyes with heterocyclic substituents and their derivatives bearing a cyanide co-ligand: NIR donor materials for vacuum-processed solar cellsJournal of Materials Chemistry, 5
M. Strobl, A. Walcher, T. Mayr, I. Klimant, S. Borisov (2017)
Trace Ammonia Sensors Based on Fluorescent Near-Infrared-Emitting aza-BODIPY Dyes.Analytical chemistry, 89 5
Xin-Dong Jiang, Jiuli Zhao, Qian Li, Chang-Liang Sun, J. Guan, G.-T. Sun, Lin-jiu Xiao (2016)
Synthesis of NIR fluorescent thienyl-containing aza-BODIPY and its application for detection of Hg2+: Electron transfer by bonding with Hg2+Dyes and Pigments, 125
Hua Lu, Soji Shimizu, J. Mack, Zhen Shen, N. Kobayashi (2011)
Synthesis and spectroscopic properties of fused-ring-expanded aza-boradiazaindacenes.Chemistry, an Asian journal, 6 4
R. Priefer, J. Griffiths, Janelle Ludwig, G. Skelhorne-Gross, R. Greene (2011)
Synthesis of Aza-BODIPY Boron Difluoride PDT Agents to Promote Apoptosis in HeLa CellsLetters in Organic Chemistry, 8
J. Killoran, S. McDonnell, J. Gallagher, D. O’Shea (2008)
A substituted BF2-chelated tetraarylazadipyrromethene as an intrinsic dual chemosensor in the 650–850 nm spectral rangeNew Journal of Chemistry, 32
Yuelin Liu, Jingwei Zhu, Yanmei Xu, Yu Qin, Dechen Jiang (2015)
Boronic Acid Functionalized Aza-Bodipy (azaBDPBA) based Fluorescence Optodes for the Analysis of Glucose in Whole Blood.ACS applied materials & interfaces, 7 21
Marco Grossi, Aniello Palma, S. McDonnell, Michael Hall, D. Rai, J. Muldoon, D. O’Shea (2012)
Mechanistic insight into the formation of tetraarylazadipyrromethenes.The Journal of organic chemistry, 77 20
Yu Yan, Jiangwei Tian, Fengrui Hu, Xiaoyong Wang, Zhen Shen (2016)
A near IR photosensitizer based on self-assembled CdSe quantum dot-aza-BODIPY conjugate coated with poly(ethylene glycol) and folic acid for concurrent fluorescence imaging and photodynamic therapyRSC Advances, 6
S. Kraner, Johannes Widmer, J. Benduhn, E. Hieckmann, Till Jägeler-Hoheisel, Sascha Ullbrich, D. Schütze, K. Radke, G. Cuniberti, F. Ortmann, Melanie Lorenz-Rothe, R. Meerheim, D. Spoltore, K. Vandewal, C. Koerner, K. Leo (2015)
Influence of side groups on the performance of infrared absorbing aza‐BODIPY organic solar cellsphysica status solidi (a), 212
X. Ma, Xuerong Mao, Shuwei Zhang, Xiaobo Huang, Yixiang Cheng, Chengjian Zhu (2013)
Aza-BODIPY-based D–π–A conjugated polymers with tunable band gap: synthesis and near-infrared emissionPolymer Chemistry, 4
Weili Zhao, E. Carreira (2006)
Conformationally restricted aza-BODIPY: highly fluorescent, stable near-infrared absorbing dyes.Chemistry, 12 27
J. Killoran, Lorcan Allen, J. Gallagher, W. Gallagher, D. O’Shea (2002)
Synthesis of BF2 chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behaviour.Chemical communications, 17
A. Byrne, A. Byrne, A. O'Connor, Michael Hall, J. Murtagh, K. O'Neill, K. Curran, K. Mongrain, J. Rousseau, R. Lecomte, S. McGee, J. Callanan, D. O’Shea, W. Gallagher (2009)
Vascular-targeted photodynamic therapy with BF2-chelated Tetraaryl-Azadipyrromethene agents: a multi-modality molecular imaging approach to therapeutic assessmentBritish Journal of Cancer, 101
Vusala Ibrahimova, S. Denisov, K. Vanvarenberg, P. Verwilst, V. Préat, J. Guigner, N. McClenaghan, S. Lecommandoux, C. Fustin (2017)
Photosensitizer localization in amphiphilic block copolymers controls photodynamic therapy efficacy.Nanoscale, 9 31
Jianzhang Zhao, Ke-Jing Xu, Wenbo Yang, Zhijia Wang, F. Zhong (2015)
The triplet excited state of Bodipy: formation, modulation and application.Chemical Society reviews, 44 24
Małgorzata Cyza, Arkadiusz Gut, Łukasz Łapok, J. Solarski, V. Knyukshto, M. Kępczyński, M. Nowakowska (2018)
Iodinated zinc phthalocyanine : the novel visible-light activated photosensitizer for efficient generation of singlet oxygenJournal of Photochemistry and Photobiology A-chemistry, 358
Huijing Xiang, Huijun Tham, Minh Nguyen, Soo Phua, Wei Lim, Jin‐Gang Liu, Yanli Zhao (2017)
An aza-BODIPY based near-infrared fluorescent probe for sensitive discrimination of cysteine/homocysteine and glutathione in living cells.Chemical communications, 53 37
Nagappanpillai Adarsh, R. Avirah, D. Ramaiah (2010)
Tuning photosensitized singlet oxygen generation efficiency of novel aza-BODIPY dyes.Organic letters, 12 24
M. Frenette, M. Hatamimoslehabadi, Stephanie Bellinger-Buckley, S. Laoui, Seema Bag, Olivier Dantiste, J. Rochford, C. Yelleswarapu (2014)
Nonlinear optical properties of multipyrrole dyes.Chemical physics letters, 608
C. Cardona, W. Li, A. Kaifer, D. Stockdale, G. Bazan (2011)
Electrochemical Considerations for Determining Absolute Frontier Orbital Energy Levels of Conjugated Polymers for Solar Cell ApplicationsAdvanced Materials, 23
V. Donyagina, Soji Shimizu, N. Kobayashi, E. Lukyanets (2008)
Synthesis of N,N-difluoroboryl complexes of 3,3′-diarylazadiisoindolylmethenesTetrahedron Letters, 49
William Gallagher, Lorcan Allen, Caroline O'shea, Tony Kenna, Michael Hall, Aoife Gorman, J. Killoran, Donal O'Shea (2005)
A potent nonporphyrin class of photodynamic therapeutic agent: cellular localisation, cytotoxic potential and influence of hypoxiaBritish Journal of Cancer, 92
Susanne Schutting, T. Jokic, M. Strobl, S. Borisov, D. Beer, I. Klimant (2015)
NIR optical carbon dioxide sensors based on highly photostable dihydroxy-aza-BODIPY dyesJournal of Materials Chemistry C, 3
Xiaokang Lv, Tingting Li, Qinghua Wu, Changjiang Yu, Lijuan Jiao, Erhong Hao (2018)
Polybrominated BOPHY Dyes: Synthesis, Reactivity, and Properties.The Journal of organic chemistry, 83 3
Nagappanpillai Adarsh, M. Krishnan, D. Ramaiah (2014)
Sensitive naked eye detection of hydrogen sulfide and nitric oxide by aza-BODIPY dyes in aqueous medium.Analytical chemistry, 86 18
A. O'Connor, W. Gallagher, A. Byrne (2009)
Porphyrin and Nonporphyrin Photosensitizers in Oncology: Preclinical and Clinical Advances in Photodynamic TherapyPhotochemistry and Photobiology, 85
P. Batat, M. Cantuel, G. Jonusauskas, L. Scarpantonio, Aniello Palma, D. O’Shea, N. McClenaghan (2011)
BF2-azadipyrromethenes: probing the excited-state dynamics of a NIR fluorophore and photodynamic therapy agent.The journal of physical chemistry. A, 115 48
Arkadiusz Gut, Łukasz Łapok, Dawid Drelinkiewicz, T. Pędziński, B. Marciniak, M. Nowakowska (2018)
Visible-Light Photoactive, Highly Efficient Triplet Sensitizers Based on Iodinated Aza-BODIPYs: Synthesis, Photophysics and Redox Properties.Chemistry, an Asian journal, 13 1
M. DeRosa (2002)
Photosensitized singlet oxygen and its applicationsCoordination Chemistry Reviews, 233
Wen-Jing Shi, P. Lo, D. Ng (2018)
Synthesis and acid-responsive spectral properties of near-infrared-absorbing donor-π-donor-type aza boron dipyrromethenesDyes and Pigments
Lei Gao, Saide Tang, Lei Zhu, G. Sauvé (2012)
Synthesis and Characterization of Azadipyrromethene-alt-p-Phenylene Ethynylene Conjugated Polymers and Their ChelatesMacromolecules, 45
R. Gawley, Hua Mao, M. Haque, John Thorne, Jennifer Pharr (2007)
Visible fluorescence chemosensor for saxitoxin.The Journal of organic chemistry, 72 6
Łukasz Łapok, Małgorzata Cyza, Arkadiusz Gut, M. Kępczyński, G. Szewczyk, T. Sarna, M. Nowakowska (2014)
Synthesis, spectroscopic properties and interaction with a liposomal membrane of a novel iodinated magnesium phthalocyanineJournal of Photochemistry and Photobiology A-chemistry, 286
Weili and, Erick Prof. (2005)
Conformationally Restricted Aza-Bodipy: A Highly Fluorescent, Stable, Near-Infrared-Absorbing Dye†Angewandte Chemie, 117
Arkadiusz Gut, Łukasz Łapok, D. Jamróz, M. Nowakowska (2017)
Synthesis of Thermally Robust, Photostable Aza‐Dipyrromethene Ligands Substituted with Nitro GroupsAsian Journal of Organic Chemistry, 6
A. Gorman, J. Killoran, C. O'Shea, T. Kenna, W. Gallagher, D. O’Shea (2004)
In vitro demonstration of the heavy-atom effect for photodynamic therapy.Journal of the American Chemical Society, 126 34
Daniel Frimannsson, Marco Grossi, J. Murtagh, F. Paradisi, D. O’Shea (2010)
Light induced antimicrobial properties of a brominated boron difluoride (BF(2)) chelated tetraarylazadipyrromethene photosensitizer.Journal of medicinal chemistry, 53 20
S. McDonnell, Michael Hall, Lorcan Allen, A. Byrne, W. Gallagher, D. O’Shea (2005)
Supramolecular photonic therapeutic agents.Journal of the American Chemical Society, 127 47
Michael Hall, S. McDonnell, J. Killoran, D. O’Shea (2005)
A modular synthesis of unsymmetrical tetraarylazadipyrromethenes.The Journal of organic chemistry, 70 14
Roland Gresser, M. Hummert, H. Hartmann, K. Leo, M. Riede (2011)
Synthesis and characterization of near-infrared absorbing benzannulated aza-BODIPY dyes.Chemistry, 17 10
Qianyun Tang, Wanyue Xiao, Chuhan Huang, Weili Si, Jinjun Shao, Wei Huang, Peng Chen, Qi Zhang, Xiaochen Dong (2017)
pH-Triggered and Enhanced Simultaneous Photodynamic and Photothermal Therapy Guided by Photoacoustic and Photothermal ImagingChemistry of Materials, 29
S. Leblebici, Luis Catane, David Barclay, Tara Olson, Teresa Chen, Biwu Ma (2011)
Near-infrared azadipyrromethenes as electron donor for efficient planar heterojunction organic solar cells.ACS applied materials & interfaces, 3 11
Arkadiusz Gut, Łukasz Łapok, D. Jamróz, A. Gorski, J. Solarski, M. Nowakowska (2017)
Photophysics and redox properties of aza-BODIPY dyes with electron-withdrawing groupsNew Journal of Chemistry, 41
Poulomi Majumdar, J. Mack, T. Nyokong (2015)
Synthesis, characterization and photophysical properties of an acenaphthalene fused-ring-expanded NIR absorbing aza-BODIPY dyeRSC Advances, 5
Bin Zou, Hui Liu, J. Mack, Sisi Wang, Jiangwei Tian, Hua Lu, Zhifang Li, Zhen Shen (2014)
A new aza-BODIPY based NIR region colorimetric and fluorescent chemodosimeter for fluorideRSC Advances, 4
P. Carloni, E. Damiani, L. Greci, P. Stipa, F. Tanfani, E. Tartaglini, M. Wozniak (1993)
On the use of 1,3-diphenylisobenzofuran (DPBF). Reactions with carbon and oxygen centered radicals in model and natural systemsResearch on Chemical Intermediates, 19
Qianyun Tang, Weili Si, Chuhan Huang, Kaikai Ding, Wei Huang, Peng Chen, Qi Zhang, Xiaochen Dong (2017)
An aza-BODIPY photosensitizer for photoacoustic and photothermal imaging guided dual modal cancer phototherapy.Journal of materials chemistry. B, 5 8
Shu-juan Liu, Zhengjian Shi, Wenjuan Xu, Huiran Yang, Na Xi, Xiangmei Liu, Qiang Zhao, Wei Huang, Wei Huang (2014)
A class of wavelength-tunable near-infrared aza-BODIPY dyes and their application for sensing mercury ionDyes and Pigments, 103
A series of aza‐BODIPY dyes substituted with meta‐(dimethylamino)phenyl groups were synthesized and their spectroscopic, photophysical, and electrochemical properties were compared. Highly desirable photophysical and photochemical properties were induced in meta‐(Me2N)Ph‐substituted aza‐BODIPY by bromination of the aromatic rings at the 3 and 5 positions. In particular, high values of singlet oxygen quantum yields (ΦΔ) were measured, ranging from 0.36 to 0.58. The photosensitized oxygenation process of a model compound – diphenylisobenzofuran (DPBF) ‐ proceeds via a Type II mechanism for the di‐bromo derivative, while for the tetra‐bromo derivative a mixed mechanism involving both 1O2 and other reactive forms of oxygen formation (Type I and/or Type III) was detected. Nanosecond laser photolysis experiments of the brominated aza‐BODIPYs revealed T1→Tn absorption spanning from ca. 350 nm to ca. 510 nm with the triplet lifetimes (τT) ranged between 15.6 μs and 26.0 μs. The brominated aza‐BODIPYs studied exhibited an absorption band within the so‐called “therapeutic window”, with λabs located between 620 nm and 636 nm. As estimated by CV/DPV measurements, the meta‐(Me2N)Ph‐substituted aza‐BODIPYs studied exhibited a multi‐electron oxidation processes at a relatively low oxidation potentials (Eox), pointing to the very good electron‐donating properties of these molecules. All compounds studied exhibited extremely high photostability and thermal stability.
Asian Journal of Organic Chemistry – Wiley
Published: Oct 1, 2019
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