3-Alkynylindoles as Building Blocks for the Synthesis of Electronically Tunable Indole-Based Push-Pull Chromophores.

ABSTRACT: In this study, two different classes of push-pull chromophores were synthesized in modest to excellent yields by formal [2+2] cycloaddition-retroelectrocyclization (CA-RE) reactions. N-Methyl indole was introduced as a new donor group to activate alkynes in the CA-RE transformations. Depending on the side groups' size and donor/acceptor characteristics, N-methyl indole-containing compounds exhibited λ_max values ranging between 378 and 658 nm. The optoelectronic properties of the reported D-A-type structures were studied by UV/vis spectroscopy and computational studies. The complete regioselectivity observed in the products was elaborated by one-dimensional (1D) and two-dimensional (2D) NMR studies, and the electron donor strength order of N-alkyl indole and

SUBMITTER: Erden K 

PROVIDER: S-EPMC8938952 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature