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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.

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 ?-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 ?-?* transitions.

SUBMITTER: Khalili G 

PROVIDER: S-EPMC6832541 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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Synthesis and Density Functional Theory Studies of Azirinyl and Oxiranyl Functionalized Isoindigo and (3<i>Z</i>,3'<i>Z</i>)-3,3'-(ethane-1,2-diylidene)bis(indolin-2-one) Derivatives.

Khalili Gholamhossein G   McCosker Patrick M PM   Clark Timothy T   Keller Paul A PA  

Molecules (Basel, Switzerland) 20191010 20

The design and synthesis of functionalized isoindigo compounds by reaction of isoindigo with (<i>S</i>)-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. (3<i>Z</i>,3'<i>Z</i>)-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 cor  ...[more]

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