Abstract
2-Anthrylethylene derivatives 1 E–5 E and 1 Z are synthesized to study the cis-trans photoisomerization. Interestingly, unlike 9-anthrylethylene derivatives, 2-anthrylethylene derivatives 1 E to 5 E do not exhibit E(trans) to Z (cis) photoisomerization upon direct and triplet sensitization. One-way Z (cis) to E (trans) photoisomerization of 1 Z is found to be very efficient under direct and triplet sensitization conditions, demonstrating the involvement of both singlet and triplet states. 1 E–5 E exhibits excitation wavelength dependent fluorescence indicating the existence of conformers (rotamers) at room temperature, which is confirmed by fluorescence lifetimes measurements of compounds 1 E and 2 E. Theoretical studies are carried out at DFT and ab initio methodology and the calculated relative energy difference of the conformers is very small; it ranges between 2.9 kJ·mol−1 to 6.3 kJ·mol−1 for both ground and excited states.
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Original Russian Text Copyright © 2012 by U. Srinivas, P. Arun Kumar, Kolupula Srinivas, K. Bhanuprakash, V. Jayathirtha Rao
The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 53, No. 5, pp. 872–886, September–October, 2012.
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Srinivas, U., Arun Kumar, P., Srinivas, K. et al. Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation. J Struct Chem 53, 851–865 (2012). https://doi.org/10.1134/S0022476612050058
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DOI: https://doi.org/10.1134/S0022476612050058