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Issue 15, 2017
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Substituent-sensitive fluorescence of sequentially N-alkylated tetrabenzotetraaza[8]circulenes

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Abstract

We explore the use of substituent-sensitive balance between fluorescence and non-radiative decay as a tool for optical tuning of promising materials for organic light emitting diode applications. A series of N-butylated tetrabenzotetraaza[8]circulenes is studied computationally in order to explain the gradual decrease of fluorescence intensity with the increase of the substituent number. The inter-system crossing probability is found to increase upon the gradual substitution of the circulene macrocycle as a result of the decrease of the S1–T1 energy gap due to the deformation of the tetrabenzotetraaza[8]circulenes and therefore the distortion of the π-conjugation within the macrocycles. In contrast, the S1–T1 spin–orbit coupling matrix elements are quite insensitive to the number of outer substituents. As a result, the fluorescence-responsible ππ* transition becomes less intense and the fluorescence rate constant decreases.

Graphical abstract: Substituent-sensitive fluorescence of sequentially N-alkylated tetrabenzotetraaza[8]circulenes

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Publication details

The article was received on 10 May 2017, accepted on 16 Jun 2017 and first published on 19 Jun 2017


Article type: Paper
DOI: 10.1039/C7NJ01599B
Citation: New J. Chem., 2017,41, 7621-7625
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    Substituent-sensitive fluorescence of sequentially N-alkylated tetrabenzotetraaza[8]circulenes

    G. V. Baryshnikov, R. R. Valiev, B. F. Minaev and H. Ågren, New J. Chem., 2017, 41, 7621
    DOI: 10.1039/C7NJ01599B

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