Bicyclic-Ammonium-Incorporated Ylidic Nitrogen Groups for Strong π-Electron Donation in Push-Pull Benzene π-Conjugated Systems.

Autor: Fujita H; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Arai T; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Kuchiki N; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan., Kunishima M; Faculty of Pharmaceutical Sciences, Institute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.; Faculty of Pharmaceutical Sciences, Kobe Gakuin University, 1-1-3 minatojima, Chuo-ku, Kobe, Hyogo 650-8586, Japan.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Sep 06; Vol. 26 (35), pp. 7313-7317. Date of Electronic Publication: 2024 Aug 26.
DOI: 10.1021/acs.orglett.4c02378
Abstrakt: Ylidic nitrogen-based π-electron-donating groups, (quinuclidinio)amidyl (QA) and (1-azanorbornanio)amidyl (ANA) groups, were developed to shift the absorption of push-pull benzenes toward longer wavelengths. Changing the pyrrolidinyl group to the QA or ANA group achieved a bathochromic shift of 45-100 nm in the maximum absorption wavelength, depending on the push-pull π-conjugated system investigated ( p -nitrobenzene, 1,8-naphthalimide, and an azo dye).
Databáze: MEDLINE