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A computational study of aromaticity and photophysical properties of unsymmetrical azatrioxa[8]circulenes
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Bogdan Khmelnitsky National University, Ukraine; Tomsk State University, Russian Federation.ORCID iD: 0000-0002-0716-3385
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Tomsk State University, Russian Federation; Tomsk Polytechnic University, Russian Federation.
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology. Bogdan Khmelnitsky National University, Ukraine; Tomsk State University, Russian Federation.
KTH, School of Biotechnology (BIO), Theoretical Chemistry and Biology.ORCID iD: 0000-0002-1763-9383
2017 (English)In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 41, no 7, 2717-2723 p.Article in journal (Refereed) Published
Abstract [en]

Owing to their potential use in organic light-emitting diodes and field-effect transistors we present a theoretical study of a series of unsymmetrical azatrioxa[8]circulenes in order to explain the impact of outer substituents and benzoannelation on photophysical constants and aromaticity of these compounds in terms of spin-orbit coupling perturbation and magnetically-induced ring currents. It is argued that the S1-Tn inter-system crossing processes constitute the main deactivation pathways for the fluorescence quenching, something that is supported by a good agreement obtained with experimental data on fluorescence quantum yields. The concept of the gauge-including magnetically induced currents has been applied in order to estimate the role of substituents and benzoannelated fragments on the aromaticity and particularly on the overall balance between the diatropic “aromatic” and paratropic “antiaromatic” current strengths. While a variation of the substituents in the outer perimeter of the studied circulenes does not provide a clear effect on their aromaticity, it is demonstrated that an additional benzoannelation (π-extension) of the azatrioxa[8]circulene macrocycle induces a significant aromaticity enhancement.

Place, publisher, year, edition, pages
Royal Society of Chemistry , 2017. Vol. 41, no 7, 2717-2723 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-207398DOI: 10.1039/c6nj03925aISI: 000401528400021ScopusID: 2-s2.0-85016316941OAI: oai:DiVA.org:kth-207398DiVA: diva2:1106705
Note

Funding details: 0115U000637, MESU, Ministry of Education and Science of Ukraine; Funding text: The calculations were performed using the computational resources provided by the Swedish National Infrastructure for Computing (SNIC) at the Parallel Computer Center (PDC) through the project “Multiphysics Modeling of Molecular Materials” SNIC 020/11-23. This work has been supported by the Academy of Finland through project 275845. CSC, Finnish IT Center for Science, is acknowledged for computer time. This research was also supported by the Ministry of Education and Science of Ukraine (project number 0115U000637).

QC 20170608

Available from: 2017-06-08 Created: 2017-06-08 Last updated: 2017-06-08Bibliographically approved

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