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
Khalili G, McCosker PM, Clark T, Keller PA (2019)
Publication Type: Journal article
Publication year: 2019
Journal
Book Volume: 24
Article Number: 3649
Journal Issue: 20
DOI: 10.3390/molecules24203649
Abstract
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.
Authors with CRIS profile
Involved external institutions
Australia (AU)How to cite
APA:
Khalili, G., McCosker, P.M., Clark, T., & Keller, P.A. (2019). 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, 24(20). https://doi.org/10.3390/molecules24203649
MLA:
Khalili, Gholamhossein, et al. "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 24.20 (2019).
BibTeX: Download