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Structures and photophysical properties of 3,4-diaryl-1H-pyrrol-2,5-diimines and 2,3-diarylmaleimides Full article

Journal Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014
Output data Year: 2017, Volume: 1146, Pages: 554-561 Pages count : 8 DOI: 10.1016/j.molstruc.2017.06.048
Authors Afanasenko Anastasiia M. 1,2 , Boyarskaya Dina V. 1 , Boyarskaya Irina A. 1 , Chulkova Tatiana G. 1 , Grigoriev Yakov M. 1 , Kolesnikov Ilya E. 1 , Avdontceva Margarita S. 1 , Panikorovskii Taras L. 1 , Panin Andrej I. 1 , Vereshchagin Anatoly N. 3 , Elinson Michail N. 3
Affiliations
1 Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg, 199034, Russia
2 Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands
3 N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky Prospect, Moscow, 119991, Russia

Abstract: Structural features of 3,4-diaryl-1H-pyrrol-2,5-diimines and their derivatives have been studied by molecular spectroscopy techniques, single-crystal X-ray diffraction, and DFT calculations. According to the theoretical calculations, the diimino tautomeric form of 3,4-diaryl-1H-pyrrol-2,5-diimines is more stable in solution than the imino-enamino form. We also found that the structurally related 2,3-diarylmaleimides exist in the solid state in the dimeric diketo form. 3,4-Diaryl-1H-pyrrol-2,5-diimines and 2,3-diarylmaleimides exhibit fluorescence in the blue region of the visible spectrum. The fluorescence spectra have large Stokes shifts. Aryl substituents at the 3,4-positions of 1H-pyrrol-2,5-diimine do not significantly affect fluorescence properties. The insertion of donor substituents into 2,3-diarylmaleimides leads to bathochromic shift of emission bands with hyperchromic effect.
Cite: Afanasenko A.M. , Boyarskaya D.V. , Boyarskaya I.A. , Chulkova T.G. , Grigoriev Y.M. , Kolesnikov I.E. , Avdontceva M.S. , Panikorovskii T.L. , Panin A.I. , Vereshchagin A.N. , Elinson M.N.
Structures and photophysical properties of 3,4-diaryl-1H-pyrrol-2,5-diimines and 2,3-diarylmaleimides
Journal of Molecular Structure. 2017. V.1146. P.554-561. DOI: 10.1016/j.molstruc.2017.06.048 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000406985800066
Scopus: 2-s2.0-85020824501
OpenAlex: W2626472832
Citing:
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OpenAlex 12
Scopus 12
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