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

Gleb V. Baryshnikov, Rashid R. Valiev, Boris F. Minaev, Hans Ågren

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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.

Original languageEnglish
Pages (from-to)7621-7625
Number of pages5
JournalNew Journal of Chemistry
Volume41
Issue number15
DOIs
Publication statusPublished - 2017

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

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