Journal of Chemical Sciences

, Volume 129, Issue 2, pp 223–237 | Cite as

Triphenylamine corrole dyads: Synthesis, characterization and substitution effect on photophysical properties

REGULAR ARTICLE
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Abstract

We present our results on the effect of substitution on the photophysical properties of donor-acceptor (D-A) systems in which triphenylamine is the donor and substituted corroles i.e., 5,15-phenyl-10-triphenylaminecorrole TPACor 1, 5,15-di(3,5-ditertbutylphenyl)-10-triphenylaminecorrole TPACor 2, and 5,15-(4-nitrophenyl)-10-triphenylaminecorrole TPACor 3 is the acceptor. All three dyads have been characterized by elemental analysis, MALDI-MS, cyclic voltammetry, UV-Vis and fluorescence (steady state and time-resolved) spectroscopies. Both Soret and Q bands of TPACor 3 are red-shifted when compared to other two dyads due to the presence of electron withdrawing nitro group. Similarly, redox properties of TPACor 3 are altered, when correlated to TPACor 1 and TPACor 2 dyads. However, the fluorescence emission of triphenylamine in all three dyads was quenched significantly (>90%) compared to its monomeric unit. The presence of either electron releasing or electron withdrawing group on corrole moiety has not much effect on the photophysical properties. The quenched emission was attributed to intramolecular excitation energy transfer and the photoinduced electron transfer reactions contested in these dyads.

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Graphical Abstract

Intramolecular photoinduced reactions were monitored in three 5,15-diaryl-10-triphenylaminecorroles, represented as TPACor 1 (phenyl), TPACor 2 (3,5-ditertiarybutylphenyl), and TPACor 3 (p-nitrophenyl). In these dyad systems, energy transfer from triphenylamine to corrole is the major pathway, which is explained with optical, electrochemical, and DFT studies.

Keywords

Triphenylamine corrole dyad intramolecular energy transfer time-resolved fluorescence. 
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Notes

Acknowledgements

We are grateful to Department of Science and Technology for financial support for this work (DST SB/S1/IC-14/2014). KS thanks UGC for a research fellowship.

Supplementary material

12039_2016_1219_MOESM1_ESM.doc (21 mb)
(DOC 21.0 MB)

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Copyright information

© Indian Academy of Sciences 2017

Authors and Affiliations

  1. 1.Inorganic & Physical Chemistry DivisionCSIR-Indian Institute of Chemical TechnologyTelanganaIndia

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