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Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives

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School of Chemistry and Molecular Biosciences, Molecular Horizons, Illawarra Health and Medical Research Institute University of Wollongong, Wollongong, New South Wales 2522, Australia
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Chemistry Department, Bushehr Branch, Islamic Azad University, PO Box 7519619555 Bushehr, Iran
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Department of Chemistry and Pharmacy, Computer-Chemistry-Center (CCC), Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Nägelsbachstrasse 25, 91052 Erlangen, Germany
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(20), 3649; https://doi.org/10.3390/molecules24203649
Received: 6 September 2019 / Revised: 9 October 2019 / Accepted: 9 October 2019 / Published: 10 October 2019
(This article belongs to the Special Issue Indole Derivatives: Synthesis and Application)
The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (S)-glycidyl tosylate, epibromohydrin, 2-(bromomethyl)-1-(arylsulfonyl)aziridine, and 2-(bromomethyl)-1-(alkylsulfonyl)aziridine in the presence of MeONa proceed under mild conditions in moderate yields. (3Z,3’Z)-3,3’-(Ethane-1,2-diylidene)bis(1-(oxiran-2-ylmethyl)indolin-2-one), with an extended central olefin π-conjugated moiety was also reacted with methyl-oxiranes to give the corresponding N,N’-disubstituted derivative. Calculations with DFT and TD-DFT of hypothetical isoindigo-thiophene DA molecules with various electron withdrawing substituents, including aziridine, oxirane, nitrile, carbonyl, and sulfonate, indicated that the proximity and strength of the functional group have a significant effect on the HOMO, LUMO, vertical excitation energy, and oscillator strength of the π–π* transitions. View Full-Text
Keywords: isoindigo alkylation; organic semiconductor; donor–acceptor functionalization; density functional theory; time dependent density functional theory isoindigo alkylation; organic semiconductor; donor–acceptor functionalization; density functional theory; time dependent density functional theory
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MDPI and ACS Style

Khalili, G.; McCosker, P.M.; Clark, T.; Keller, P.A. Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3Z,3’Z)-3,3’-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives. Molecules 2019, 24, 3649.

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