Synthesis of chromophores based on the hydrazinylidene cyclic acceptor moieties via the reaction of organolithium reagents with diazo compounds

Synthesis of chromophores based on the hydrazinylidene cyclic acceptor moieties via the reaction of organolithium reagents with diazo compounds Full article

Journal

Dyes and Pigments
ISSN: 1873-3743 , E-ISSN: 0143-7208

Output data

Year: 2019, Volume: 170, Article number : 107589, Pages count : DOI: 10.1016/j.dyepig.2019.107589

Authors

Trainov Konstantin P. ¹ , Litvinenko Veronika V. ^2,1 , Salikov Rinat F. ¹ , Platonov Dmitry N. ¹ , Tomilov Yury V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, 119991 Moscow, Russian Federation
2	Higher Chemical College of Russian Academy of Sciences, Dmitry Mendeleev University of Chemical Technology of Russia, Miusskaya Sq. 9, Moscow, 125047, Russian Federation

An approach to the synthesis of D-A chromophores containing hydrazinylidene cyclic acceptor moieties via the reaction of organolithium reagents with cyclic diazo compound precursors was developed. In contrast to conventional approaches the new one allows to introduce thiophene fragments into a chromophore molecule which is important for the better molecular planarity. The approach demonstrated convenience for the synthesis of hydrazinylidenecyclopentadiene, hydrazinylidenebarbituric and hydrazinylideneindanedione chromophores and a series of hydrazonocyclopentadienes with various aromatic and heterocyclic substituents were synthesized. The products demonstrated intense absorption of visible light with absorption maxima within 373–562 nm and extinction coefficients up to 36500 М−1⋅cm−1. Importantly, previously unavailable thiophenylhydrazones displayed longer wavelength absorption maxima and higher extinction coefficients relative to conventional arylhydrazones.

Trainov K.P. , Litvinenko V.V. , Salikov R.F. , Platonov D.N. , Tomilov Y.V.
Synthesis of chromophores based on the hydrazinylidene cyclic acceptor moieties via the reaction of organolithium reagents with diazo compounds
Dyes and Pigments. 2019. V.170. 107589 . DOI: 10.1016/j.dyepig.2019.107589 WOS Scopus OpenAlex

≡ Web of science:	WOS:000478711200057
≡ Scopus:	2-s2.0-85066809257
≡ OpenAlex:	W2947209950