Design and synthesis of new functionalized isoindigo and (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) derivatives

Abstract

Design and synthesis of new functionalized isoindigo and (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) derivatives

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

“…It is an electron-deficient moiety, as indicated by low highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies, essential for small bandgap DA systems [10]. Furthermore, isoindigo features NH functionalities, which are easily alkylated, allowing facile derivative synthesis [13,14]. This method has been employed to modify a variety of DA systems that have been noted to influence solubility, aggregation, light absorption, blend morphology, charge-carrier mobility, stability, and electronic properties [11,12,15,16,17,18,19,20,21,22,23,24].…”

Synthesis of 3,3’‐(Ethane‐1,2‐diylidene)bis(indolin‐2‐one) Promoted by Thermally‐activated Electron Transfer and Photoreduction of CO2 to CH4 and CO

“…Two approaches have been reported. One is through the reaction of oxindole and glyoxal in the presence of HCl and methanol (Scheme S6, Supporting Information) [44] . The other is through the reaction of isatin and propionic anhydride in pyridine (Scheme S7, Supporting Information) [45] .…”

“…One is through the reaction of oxindole and glyoxal in the presence of HCl and methanol (Scheme S6, Supporting Information). [44] The other is through the reaction of isatin and propionic anhydride in pyridine (Scheme S7, Supporting Information). [45] In our approach, the construction of EBI and the Sonogashira coupling can be accomplished without mutual interference in one pot (The optimal isolated yield of C was 52 %, Scheme S4, Supporting Information).…”

The Synthesis and Theoretical Investigation of Functionalized N,N′‐Arylthioalkylisoindigo Derivatives

“…As part of our program directed toward the development of novel methods to construct isoindigo derivatives, [17,18] we previously developed a new synthesis of various N , N ′‐dialkylisoindigos using sodium methoxide as the base under mild condition [19] . The current studies started with the substituted thiourea compounds 2 as substrates as there is precedent for S ‐thiolation of bromoalkylisoindigo as these sulfur‐containing compounds are effective nucleophiles in the presence of sodium methoxide.…”