TY - JOUR
T1 - Dibenzoarsepins
T2 - Planarization of 8π-Electron System in the Lowest Singlet Excited State
AU - Kawashima, Ikuo
AU - Imoto, Hiroaki
AU - Ishida, Masatoshi
AU - Furuta, Hiroyuki
AU - Yamamoto, Shunsuke
AU - Mitsuishi, Masaya
AU - Tanaka, Susumu
AU - Fujii, Toshiki
AU - Naka, Kensuke
N1 - Funding Information:
The work in Kyoto was supported by JSPS KAKENHI, grant number JP17H04577 (Coordination Asymmetry), to H.I. The work in Kyushu was supported by JSPS KAKENHI, grant numbers JP19H04586 and JP19K05439, to M.I. The work in Tohoku was supported by the Research Program of “Five-star Alliance” in “NJRC Mater. & Dev.”
Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2019/8/19
Y1 - 2019/8/19
N2 - 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 (S1) state. The computational approach for the assessment of the aromatic indices revealed that the dibenzoarsepins studied show aromaticity (8π system) in the S1 states in line with Baird's rule. The lone pair electrons of the arsenic atoms play a crucial role in the aromaticity in the S1 states.
AB - 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 (S1) state. The computational approach for the assessment of the aromatic indices revealed that the dibenzoarsepins studied show aromaticity (8π system) in the S1 states in line with Baird's rule. The lone pair electrons of the arsenic atoms play a crucial role in the aromaticity in the S1 states.
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U2 - 10.1002/anie.201904882
DO - 10.1002/anie.201904882
M3 - Article
C2 - 31251829
AN - SCOPUS:85069882380
SN - 1433-7851
VL - 58
SP - 11686
EP - 11690
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 34
ER -