May 20, 2019
Mechanochromism, Twisted/Folded Structure Determination, and Derivatization of (N-Phenylfluorenylidene)acridane
Angewandte Chemie International Edition
- ,
- ,
- ,
- ,
- Volume
- 58
- Number
- 26
- First page
- 8762
- Last page
- 8767
- Language
- English
- Publishing type
- Research paper (scientific journal)
- DOI
- 10.1002/anie.201902636
- Publisher
- Wiley
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim (N-Phenylfluorenylidene)acridane (Ph-FA) compounds with electron-withdrawing and -donating substituents (H, MeO, Ph, NO2, 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-NO2-C6H4-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.
- Link information
-
- DOI
- https://doi.org/10.1002/anie.201902636
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/30983037
- URL
- http://orcid.org/0000-0001-9084-9670
- Scopus
- https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85066082983&origin=inward
- Scopus Citedby
- https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85066082983&origin=inward
- ID information
-
- DOI : 10.1002/anie.201902636
- ISSN : 1433-7851
- eISSN : 1521-3773
- ORCID - Put Code : 57594285
- Pubmed ID : 30983037
- SCOPUS ID : 85066082983