2,2′-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins

Artur J. Moro, A. Jorge Parola, Fernando Pina, Ana Maria Pana, Valentin Badea, Iulia Pausescu, Sergiu Shova, Liliana Cseh

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The chemistry of 2,2′-spirobis[chromene] derivatives is intimately related to the one of anthocyanins and similar compounds. The 2,2′-spirobis[chromene] species plays a central role in the network of chemical reactions connecting two different flavylium-based multistate systems. In the present work, a new asymmetric 2,2′-spirobis[chromene] intermediate possessing a constrained propylenic bridge between carbons 3 and 3′ was isolated and its role as a pivot in the anthocyanins-type multistate of chemical reactions was investigated by the conjugation of absorption spectroscopy, stopped-flow, NMR, and X-ray crystallography. It was confirmed that the propylenic bridge is essential to stabilize the spirobis[chromene] species. Furthermore, under acidic conditions, two cis-trans styrylflavylium isomers were identified, which could be interconverted directly into one another with light. This is the first report of styrylflavylium cations with photoisomerization on the styryl moiety.

Original languageEnglish
Pages (from-to)5301-5309
Number of pages9
JournalJournal of Organic Chemistry
Volume82
Issue number10
DOIs
Publication statusPublished - 19 May 2017

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