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Novel photoresponsive cyclicparaphenylenediazenes: structure, strain energy, cistrans isomerization, and electronic properties

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Abstract

A series of cistrans 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 cistrans-[3]CPPD, seven isomers of cistrans-[4]CPPD, eleven isomers of cistrans-[5]CPPD, and sixteen isomers of cistrans-[6]CPPD have been proposed using density functional theory (DFT) at the B3LYP/6-31+G(d,p) level of theory. The stability of these CPPDs has been quantified by the 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 Image ID:c8pp00502h-t1.gif of cistrans-CPPDs were also compared with those of all-cis-CPPDs and all-trans-CPPD isomers. The calculations suggest that cistrans-CPPDs are more stable than all-cis and all-trans-CPPDs. The SE and Image ID:c8pp00502h-t2.gif 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 cistrans-CPPDs indicate that these oligomers 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, and thermochemical and electronic properties can be a good starting point for the synthesis of CPPD-based photoswitchable and solar fuel cell devices.

Graphical abstract: Novel photoresponsive cyclicparaphenylenediazenes: structure, strain energy, cis–trans isomerization, and electronic properties

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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, Advance Article

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    Novel photoresponsive cyclicparaphenylenediazenes: structure, strain energy, cistrans isomerization, and electronic properties

    M. Akbar Ali and M. A. Alam, Photochem. Photobiol. Sci., 2019, Advance Article , DOI: 10.1039/C8PP00502H

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