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Structure and Photophysical Properties of 1,1,2,2‐Tetra(1‐anthryl)ethane: A C(sp3)−C(sp3) Bond Substituted with Four Anthracene Units

Structure and Photophysical Properties of 1,1,2,2‐Tetra(1‐anthryl)ethane: A C(sp3)−C(sp3) Bond... The title aromatic compound comprising four anthracene units was synthesized by the McMurry coupling of di(1‐anthryl) ketone as a hydrogenated product in 65 % yield. The molecule forms a C2 symmetric structure with the ap conformation about the C(sp3)−C(sp3) single bond, as revealed by X‐ray analysis and DFT calculations. The UV/vis and fluorescence spectra of this compound were compared with those of anthracene, di(1‐anthryl)methane, and 1,2‐di(1‐anthryl)ethane. The fluorescence spectrum showed a broad emission band at 450 nm having a long lifetime at 21 ns, which was assignable to an excimer‐type emission, in contrast to the other reference compounds. The characteristic photophysical property is discussed in terms of the molecular structure with the aid of the noncovalent interaction plots and the conformational analysis. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

Structure and Photophysical Properties of 1,1,2,2‐Tetra(1‐anthryl)ethane: A C(sp3)−C(sp3) Bond Substituted with Four Anthracene Units

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References (2)

Publisher
Wiley
Copyright
© 2022 Wiley‐VCH GmbH
eISSN
2192-6506
DOI
10.1002/cplu.202100447
Publisher site
See Article on Publisher Site

Abstract

The title aromatic compound comprising four anthracene units was synthesized by the McMurry coupling of di(1‐anthryl) ketone as a hydrogenated product in 65 % yield. The molecule forms a C2 symmetric structure with the ap conformation about the C(sp3)−C(sp3) single bond, as revealed by X‐ray analysis and DFT calculations. The UV/vis and fluorescence spectra of this compound were compared with those of anthracene, di(1‐anthryl)methane, and 1,2‐di(1‐anthryl)ethane. The fluorescence spectrum showed a broad emission band at 450 nm having a long lifetime at 21 ns, which was assignable to an excimer‐type emission, in contrast to the other reference compounds. The characteristic photophysical property is discussed in terms of the molecular structure with the aid of the noncovalent interaction plots and the conformational analysis.

Journal

ChemPlusChem – Wiley

Published: Jan 1, 2022

Keywords: anthracene; excimers; fluorescence; McMurry coupling; pi interactions

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