The impact of the molecular structure on aggregation and solid state luminescence of 2,3-diarylfumaronitriles

The impact of the molecular structure on aggregation and solid state luminescence of 2,3-diarylfumaronitriles Full article

Journal

Journal of Molecular Structure
ISSN: 0022-2860 , E-ISSN: 1872-8014

Output data

Year: 2022, Volume: 1248, Article number : 131503, Pages count : DOI: 10.1016/j.molstruc.2021.131503

Authors

Afanasenko Anastasiia M. ¹ , Krutin Danil V. ² , Taishev Artur E. ² , Novikov Alexander S. ² , Chulkova Tatiana G. ³ , Kolesnikov Ilya E. ² , Kornyakov Ilya V. ² , Panikorovskii Taras L. ² , Vereshchagin Anatoly N. ⁴ , Elinson Michail N. ⁴

Affiliations

1	Department of Chemistry, McGill University, Otto Maass Chemistry Building, 801 Sherbrooke Street, West Montreal, Quebec H3A0B8, Canada
2	Saint Petersburg State University, 7/9 Universitetskaya Nab., Saint Petersburg 199034 Russia
3	Institute of Macromolecular Compounds, Russian Academy of Sciences, 31 Bolshoy pr., Saint Petersburg 199004 Russia
4	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow 119991 Russia

This work focuses on the substituent effect in 2,3-diarylfumaronitriles on the optical properties and intermolecular interactions in the solid state. 2,3-Diarylfumaronitriles show various luminescence behaviour in solution and in the solid state. Aggregation patterns of 2,3-diarylfumaronitriles govern their luminescent properties in the solid state. The weak intermolecular interactions Ntriple bondC···Ntriple bondC, C–H···Cl, and C–H···Ntriple bondC were detected in the X-ray structures of 2,3-diarylfumaronitriles and studied by DFT calculations at the M06–2X/6–311++G(d,p) level of theory and topological analysis of the electron density distribution within the framework of QTAIM method. The estimated strength of these non-covalent bonds is 0.8–1.3 kcal/mol. The orientation of molecules in crystals depends on the substituents in 2,3-diarylfumaronitriles. Distinct molecular orientation and packing arrangements in crystalline 2,3-diarylfumaronitriles ensured perturbed electronic communication amongst the nearest and non-nearest molecules through an interplay of excimer and dipole couplings. As a result, the intermolecular interactions govern the solid state luminescence of molecules.

Afanasenko A.M. , Krutin D.V. , Taishev A.E. , Novikov A.S. , Chulkova T.G. , Kolesnikov I.E. , Kornyakov I.V. , Panikorovskii T.L. , Vereshchagin A.N. , Elinson M.N.
The impact of the molecular structure on aggregation and solid state luminescence of 2,3-diarylfumaronitriles
Journal of Molecular Structure. 2022. V.1248. 131503 . DOI: 10.1016/j.molstruc.2021.131503 WOS Scopus OpenAlex

Web of science:	WOS:000703670300014
Scopus:	2-s2.0-85115306911
OpenAlex:	W3200198034

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