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Mechanochromism, Twisted/Folded Structure Determination, and Derivatization of ( N ‐Phenylfluorenylidene)acridane
Author(s) -
Matsuo Yutaka,
Wang Ya,
Ueno Hiroshi,
Nakagawa Takafumi,
Okada Hiroshi
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201902636
Subject(s) - moiety , conformational isomerism , chemistry , protonation , substituent , aryl , derivatization , thermochromism , photochemistry , crystallography , stereochemistry , molecule , organic chemistry , high performance liquid chromatography , alkyl , ion
Abstract (N‐Phenylfluorenylidene)acridane (Ph‐FA) compounds with electron‐withdrawing and ‐donating substituents (H, MeO, Ph, NO 2 , Br, F) at the para position of the phenyl group were successfully synthesized by Barton–Kellogg reactions of N ‐aryl thioacridones and diazofluorene. By using the substituent on the nitrogen atom to alter the electronic properties, both the folded and twisted conformers of p ‐NO 2 ‐C 6 H 4 ‐FA could be crystallographically characterized, which enabled the charge transfer from the electron‐donating acridane moiety to the electron‐accepting fluorenylidene moiety to be understood. Ground‐state mechanochromism, thermochromism, vapochromism, and proton‐induced chromism were demonstrated between the folded and twisted conformations of the conformers. Protonation and chemical oxidation of Ph‐FA gave two stable acridinium compounds, namely, the fluorenylacridinium and acridinium radical cations. The present study will contribute to the development of functional dyes and organic semiconductors.