Synthesis and UV–vis spectra of a new type of dye via a decarboxylative azo coupling reaction

Synthesis and UV–vis spectra of a new type of dye via a decarboxylative azo coupling reaction Научная публикация

Журнал

Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581

Вых. Данные

Год: 2016, Том: 57, Номер: 38, Страницы: 4311-4313 Страниц : 3 DOI: 10.1016/j.tetlet.2016.08.043

Авторы

Platonov Dmitry N. ¹ , Okonnishnikova Galina P. ¹ , Salikov Rinat F. ¹ , Tomilov Yury V. ¹

Организации

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

The azo coupling reactions between polymethoxycarbonyl(N-mesylaminovinyl)cyclopentadienyl potassium and aryldiazonium tetrafluoroborates with subsequent hydrolysis and decarboxylation of one ester group led to the formation of new polyene structures, specifically, isomeric 3- and 4-aminovinyl-5-hydrazonocyclopentadienes. The latter undergo cyclization on silica gel to give substituted 2-aryl-2H-cyclopenta[c]pyridazines. The resulting (2-arylhydrazono)cyclopenta-1,3-dienes are deep-red colored and may be of interest as dyes, particularly in dye-sensitized solar cells. The products were examined by UV–Vis spectroscopy and demonstrated large extinction co-efficients with absorption maxima in the range of 400–600 nm. The single crystal X-ray data revealed a short Nsingle bondN bond length in the hydrazones, indicating strong conjugation between the donor and acceptor parts of the molecules.

Platonov D.N. , Okonnishnikova G.P. , Salikov R.F. , Tomilov Y.V.
Synthesis and UV–vis spectra of a new type of dye via a decarboxylative azo coupling reaction
Tetrahedron Letters. 2016. V.57. N38. P.4311-4313. DOI: 10.1016/j.tetlet.2016.08.043 WOS Scopus OpenAlex

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