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Light induced intramolecular energy and electron transfer events in carbazole–corrole and phenothiazine-corrole dyads

B. Shivaprasadachary

Polymer and Functional Materials Division, Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

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A. R. Ramya

Polymer and Functional Materials Division, Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

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Govind Reddy

Polymer and Functional Materials Division, Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

Centre for Advanced Materials & Industrial Chemistry (CAMIC), School of Science, RMIT University, Melbourne VIC3000, Australia

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, and

L. Giribabu

Polymer and Functional Materials Division, Indian Institute of Chemical Technology, Hyderabad 500007, Telangana, India

Academy of Scientific and Innovative Research, CSIR-IICT, India

E-mail Address: giribabu@iict.res.in

Corresponding author.

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https://doi.org/10.1142/S1088424619501177Cited by:5 (Source: Crossref)

Abstract

We report two corrole based donor–acceptor (D–A) dyads, Cbz-Cor and Ptz-Cor to understand the energy/electron transfer reactions. In these D–A systems, the donor, either carbazole (Cbz) or phenothiazine (Ptz), is covalently connected at the meso-phenyl position of 10-(phenyl)-5,15-bis-(pentafluorophenyl)corrole (Ph-Cor) by C–N linkage. Both the dyads were characterized by ¹H NMR, MALDI-TOF MS, UV-vis, electrochemical, computational methods, study state fluorescence and TCSPC techniques. A comparison of absorption spectra with their reference monomeric compounds (Cbz-Ph, Ptz-Ph and Ph-Cor) revealed minimal ground-state interactions between chromophores in both dyads. Fluorescence studies suggested that singlet–singlet energy transfer from ¹Cbz* to corrole is the major photochemical pathway in the Cbz-Cor dyad with a quenching efficiency of $\sim$ 99%. Detailed analysis of the data suggests that Forster’s dipole–dipole mechanism does not adequately explain this energy transfer. However, at a 410 nm excitation, florescence quenching is detected in Ptz-Cor (49%) supporting a photo induced electron transfer (PET) process from the ground state of PTZ to the excited state of corrole macrocycle. The electron-transfer rates ( $k_{E T})$ of Ptz-Cor are found in the range $0.6 \times 1 0^{7}$ to $1.24 \times 1 0^{8} s^{- 1}$ and are concluded to be solvent dependent.

Dedicated to Professor Roberto Paolesse on the occasion of his 60th birthday.

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