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Dibenzoarsepins: Planarization of 8π‐Electron System in the Lowest Singlet Excited State
Author(s) -
Kawashima Ikuo,
Imoto Hiroaki,
Ishida Masatoshi,
Furuta Hiroyuki,
Yamamoto Shunsuke,
Mitsuishi Masaya,
Tanaka Susumu,
Fujii Toshiki,
Naka Kensuke
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201904882
Subject(s) - chemical mechanical planarization , aromaticity , excited state , singlet state , lone pair , electron , chemistry , photochemistry , atomic physics , physics , molecule , organic chemistry , quantum mechanics , layer (electronics)
Dibenzo[b,f]arsepins possessing severely distorted cores compared to those of other heteropins were synthesized. These derivatives exhibited dual photoluminescence in the green‐to‐red region (500–700 nm) and the near‐ultraviolet region (<380 nm), which could be attributed to the planarization of the arsepin core in the lowest singlet excited (S 1 ) state. The computational approach for the assessment of the aromatic indices revealed that the dibenzoarsepins studied show aromaticity (8π system) in the S 1 states in line with Baird's rule. The lone pair electrons of the arsenic atoms play a crucial role in the aromaticity in the S 1 states.