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

Dengiz, Çağatay
© 2022 American Chemical Society.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 λmax 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 triazene donor groups was also established. The intramolecular charge-transfer characteristics of the target push-pull chromophores were investigated by frontier orbital depictions, electrostatic potential maps, and time-dependent density functional theory calculations. Overall, the computational and experimental results match each other. Integrating a new donor group, N-alkyl indole, into the substrates used in formal [2+2] cycloaddition-retroelectrocyclizations has significant potential to overcome the limited donor-substituted substrate scope problem of CA-RE reactions.
The Journal of organic chemistry


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Citation Formats
K. ERDEN and Ç. Dengiz, “3-Alkynylindoles as Building Blocks for the Synthesis of Electronically Tunable Indole-Based Push-Pull Chromophores.,” The Journal of organic chemistry, vol. 87, no. 6, pp. 4385–4399, 2022, Accessed: 00, 2022. [Online]. Available: https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85125956796&origin=inward.