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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

Journal Article


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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.

UOW Authors


  •   Khalili, Gholamhossein (external author)
  •   McCosker, Patrick (external author)
  •   Clark, Timothy (external author)
  •   Keller, Paul

Publication Date


  • 2019

Citation


  • 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), 3649-1-3649-15.

Scopus Eid


  • 2-s2.0-85074066904

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1992&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/978

Start Page


  • 3649-1

End Page


  • 3649-15

Volume


  • 24

Issue


  • 20

Place Of Publication


  • Switzerland

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.

UOW Authors


  •   Khalili, Gholamhossein (external author)
  •   McCosker, Patrick (external author)
  •   Clark, Timothy (external author)
  •   Keller, Paul

Publication Date


  • 2019

Citation


  • 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), 3649-1-3649-15.

Scopus Eid


  • 2-s2.0-85074066904

Ro Full-text Url


  • https://ro.uow.edu.au/cgi/viewcontent.cgi?article=1992&context=smhpapers1

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers1/978

Start Page


  • 3649-1

End Page


  • 3649-15

Volume


  • 24

Issue


  • 20

Place Of Publication


  • Switzerland