Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies

Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies Full article

Journal

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

Output data

Year: 2020, Volume: 1199, Article number : 126789, Pages count : DOI: 10.1016/j.molstruc.2019.07.036

Authors

Afanasenko Anastasiia M. ^1,2 , Novikov Alexander S. ¹ , Chulkova Tatiana G. ¹ , Grigoriev Yakov M. ¹ , Kolesnikov Ilya E. ¹ , Selivanov Stanislav I. ¹ , Starova Galina L. ¹ , Zolotarev Andrey A. 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

Phenanthrene-9,10-dicarbonitriles show various luminescence behaviour in solution and in the solid state. Aggregation patterns of phenanthrene-9,10-dicarbonitriles govern their luminescent properties in the solid state. Single crystal structures of phenanthrene-9,10-dicarbonitriles showed head-to-tail intraplane (or quasi-intraplane) intermolecular interactions and π-stacking patterns with eclipsing of molecules when viewed orthogonal to the stacking plane. The π-stacking interactions were detected in the X-ray structures of phenanthrene-9,10-dicarbonitriles 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 the C⋯C contacts responsible for the π-stacking interactions is 0.6–1.1 kcal/mol. The orientation of molecules in crystals depends on the substituents in phenanthrene-9,10-dicarbonitriles. Distinct molecular orientation and packing arrangements in crystalline phenanthrene-9,10-dicarbonitriles ensured perturbed electronic communication among 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. , Novikov A.S. , Chulkova T.G. , Grigoriev Y.M. , Kolesnikov I.E. , Selivanov S.I. , Starova G.L. , Zolotarev A.A. , Vereshchagin A.N. , Elinson M.N.
Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies
Journal of Molecular Structure. 2020. V.1199. 126789 . DOI: 10.1016/j.molstruc.2019.07.036 WOS Scopus OpenAlex

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