A New Photochromic 8π-System Based on an Azaheptatriene-Tetrahydroazepinoisoquinoline Electrocyclization

Autor:	Jean Kossanyi, Véronique Wintgens, Thomas Hartmann, Yongsheng Tan, Pierre Valat, Heinz Dürr, Volker Huch
Rok vydání:	2001
Předmět:	Photochromism Chemistry Stereochemistry Organic Chemistry Flash photolysis Nanosecond Ring (chemistry) Photochemistry
Zdroj:	The Journal of Organic Chemistry. 66:1130-1137
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo000807+
Popis:	A new photochromic family of tetrahydroazepinoisoquinolines (THAI) 4a-i has been prepared. It undergoes light-induced ring opening from spiro compounds 4 to betaines 3 that decolorize in a very fast cyclizing reaction. Depending on substitution of the precursors 1 and 6, the photochromic styryltetrahydroindolizines (THI) 5k-q are formed in a periselective way. The conformation and configuration of the new photochromic THAI 4 and THI 5 were investigated by NMR and the structure of both compounds was proven by X-ray analysis. The photochromic properties were studied by laser flash photolysis, which afforded the lifetime of the colored form 3 and 3' in the micro- or nanosecond range.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c1868b7fadc9b5c0dadac3f835f46325 https://doi.org/10.1021/jo000807+ Zobrazit plný text záznamu