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Novel Photoresponsive Cyclicparaphenylenediazenes: Structure, Strain Energy, Cis-Trans Isomerization, and Electronic Properties

Abstract

A series of cis-trans isomers of cyclicparaphenylenediazenes (CPPDs) have been designed to explore their potential applications in solar thermal fuels and photoswitchable devices. In this work, three isomers of cis-trans-[3]CPPDs, seven isomers of cis-trans-[4]CPPD, eleven isomers of cis-trans-[5]CPPD, and sixteen isomers of cis-trans-[6]CPPD has been proposed using density functional theory (DFT) at B3LYP/6-31+G(d,p) level of theory. The stability of these CPPDs has been quantified by homodesmotic reaction approach. Strain energies (SE) indicate that 3-cct, 4-ctct-anti, 5-cctct-anti, and 6-cttttc-anti are stable molecules in their respective CPPDs. The SE and heats of formation ( ) of cis-trans-CPPDs were also compared with all-cis-CPPDs and all-trans-CPPDs isomers. The calculations suggest that cis-trans-CPPDs are more stable than all-cis and all-trans-CPPDs. The SE and /n also suggest that 3-cct, 4-ctct-anti, 5-cctct-anti, and 6-cttttc-anti are important candidates for laboratory test. The calculated highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO) energy gaps of cis-trans-CPPDs indicate that these oligomer are potential materials for the construction of solar cells. Time-dependent (TD) DFT calculations of CPPDs show a characteristic peak in the range of 450 nm to 600 nm, which is consistent with previous studies. The predicted structures, thermochemical, and electronic properties can be a good starting point for the synthesis of CPPDs based photoswitchable and solar fuels cell devices.

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Publication details

The article was received on 02 Nov 2018, accepted on 13 Feb 2019 and first published on 13 Feb 2019


Article type: Paper
DOI: 10.1039/C8PP00502H
Citation: Photochem. Photobiol. Sci., 2019, Accepted Manuscript

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    Novel Photoresponsive Cyclicparaphenylenediazenes: Structure, Strain Energy, Cis-Trans Isomerization, and Electronic Properties

    A. A. Mohamad and M. Alam, Photochem. Photobiol. Sci., 2019, Accepted Manuscript , DOI: 10.1039/C8PP00502H

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