Near-Infrared-Responsive Hydrocarbons Designed by p-Extension of Indeno[1,2,3,4-pgra]perylene at the 1,2,12-Positions
- Authors
- Kato, Masaki; Kim, Jinseok; Oh, Juwon; Shimizu, Daiki; Fukui, Norihito; Shinokubo, Hiroshi
- Issue Date
- Apr-2023
- Publisher
- John Wiley & Sons Ltd.
- Keywords
- C-H arylation; pi-extension; molecular design; near-infrared absorption; polycyclic aromatic hydrocarbon
- Citation
- Chemistry - A European Journal, v.29, no.23
- Journal Title
- Chemistry - A European Journal
- Volume
- 29
- Number
- 23
- URI
- https://scholarworks.bwise.kr/sch/handle/2021.sw.sch/22569
- DOI
- 10.1002/chem.202300249
- ISSN
- 0947-6539
1521-3765
- Abstract
- The relationship between the overall electronic structure of pi-conjugated molecules and the arrangement of their constituent elements is of fundamental importance. Establishing rational design guidelines for conjugated hydrocarbons with narrow HOMO-LUMO gaps is useful to develop near-infrared (NIR) responsive dyes and redox-active materials. This study describes the synthesis and properties of three conjugated hydrocarbons, i. e., an indenonaphthoperylene, an indenoterrylene, and a diindenoterrylene. These molecules exhibit NIR absorption despite the absence of significant antiaromaticity and diradical character. Notably, the indenonaphthoperylene exhibits red-to-NIR emission in the 620-850 nm region. The indenoterrylene and the diindenoterrylene exhibit NIR absorption tailing to 870 and 940 nm, respectively. Moreover, the effect of the pi-extension of indenoperylene is disclosed in order to propose guidelines for achieving a narrow HOMO-LUMO gap with negligible antiaromaticity and diradical character.
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