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- Title
Bent π-Conjugated Systems Composed of Three-Dimensional Benzoannulenes.
- Authors
Nishiuchi, Tomohiko; Iyoda, Masahiko
- Abstract
This article describes bent π-conjugated systems composed of alternating o-phenylene and Z-vinylene units. all- Z-[ n] Benzo[4 n]annulenes are higher homologues of dibenzocyclooctatetraene ( DBCOT) with a concave π system, and attempts were made to convert [20]- and [24]annulenes having partial belt structures of fullerenes and carbon nanotubes into [10]- and [12]phenacenes. A bent π-conjugated system composed of two DBCOT units showed dynamic syn- anti equilibrium in solution and behaved as dynamic molecular tweezers ( DMTs). The syn isomers of the DMTs formed blue charge-transfer complexes with DDQ in solution, and this complexation and color change were applied to thermochromism. Furthermore, DMTs having two CN groups on each COT ring exhibited crystalline-state emission in the presence of solvent molecules, although almost no emission was observed in solution or the solid state. Based on this crystalline-state emission, a vapochromic system was established. The multifunctional properties of DMTs caused by the flexibility of the nonplanar π system are summarized.
- Subjects
ETHYLENE dichloride; MAGNETIC tweezers; CRYSTALLINE lens; EMISSIONS (Air pollution); AIR pollution
- Publication
Chemical Record, 2015, Vol 15, Issue 1, p329
- ISSN
1527-8999
- Publication type
Article
- DOI
10.1002/tcr.201402079