Synthesis of spiropyrans and merocyanine dyes based on 1-benzothieno[3,2-b]pyrrole

Synthesis of spiropyrans and merocyanine dyes based on 1-benzothieno[3,2-b]pyrrole Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2009, Volume: 58, Number: 2, Pages: 380-386 Pages count : 7 DOI: 10.1007/s11172-010-0019-1

Authors

Shimkin A.A. ¹ , Shirinian V.Z. ¹ , Mailyan A.K. ¹ , Krayushkin M.M. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

A convenient method was developed for the synthesis of photochromic spiropyrans and merocyanine dyes of the 1-benzothieno[3,2-b]pyrroline series based on the conventional condensation of the analog of Fischer’s salt, viz., 1,2,3,3-tetramethyl-3H-[1]benzothieno-[3,2-b]pyrrolium triflate, with aromatic 2-hydroxyaldehydes. Unlike Fischer’s salt, benzothieno-pyrrolium salts readily undergo the [1,5]-sigmatropic rearrangement giving rise to 2H-[1]benzo-thieno[3,2-b]pyrrole derivatives. The latter compounds were used for the synthesis of the first representatives of the previously unknown spiro compounds and merocyanine dyes. The long-wavelength maxima of merocyanines of the 2H-benzothienopyrrole series are batho-chromically shifted by more than 100 nm with respect to the absorption maxima of the “classical” 3H-benzothienopyrrole analogs.

Shimkin A.A. , Shirinian V.Z. , Mailyan A.K. , Krayushkin M.M.
Synthesis of spiropyrans and merocyanine dyes based on 1-benzothieno[3,2-b]pyrrole
Russian Chemical Bulletin. 2009. V.58. N2. P.380-386. DOI: 10.1007/s11172-010-0019-1 WOS Scopus OpenAlex

Web of science:	WOS:000275907000001
Scopus:	2-s2.0-77950238502
OpenAlex:	W2032721718

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