Revisiting the Synthesis of Tetramethoxyindolo[3,2-]indole Derivatives and the Study of Their Photoinduced Radical Formation in Halogenated Solvents.

J Org Chem

Key Laboratory of Flexible Optoelectronic Materials and Technology, Ministry of Education, School of Optoelectronic Materials & Technology, Jianghan University, Wuhan 430056, P. R. China.

Published: September 2025


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Article Abstract

We previously reported that the attempt to synthesize tetramethoxyindolo[3,2-]indole led to an undefined product. Now, it is confirmed that its instability is derived from the one-electron transfer from the tetramethoxyindolo[3,2-]indole derivatives to halogenated solvents under ultraviolet-visible (UV-vis) light irradiation, forming a stable indolo[3,2-]indole radical cation while causing the carbon-halogen (C-X, X = Cl, Br, I) bond scission.

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http://dx.doi.org/10.1021/acs.joc.5c01360DOI Listing

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Revisiting the Synthesis of Tetramethoxyindolo[3,2-]indole Derivatives and the Study of Their Photoinduced Radical Formation in Halogenated Solvents.

J Org Chem

September 2025

Key Laboratory of Flexible Optoelectronic Materials and Technology, Ministry of Education, School of Optoelectronic Materials & Technology, Jianghan University, Wuhan 430056, P. R. China.

We previously reported that the attempt to synthesize tetramethoxyindolo[3,2-]indole led to an undefined product. Now, it is confirmed that its instability is derived from the one-electron transfer from the tetramethoxyindolo[3,2-]indole derivatives to halogenated solvents under ultraviolet-visible (UV-vis) light irradiation, forming a stable indolo[3,2-]indole radical cation while causing the carbon-halogen (C-X, X = Cl, Br, I) bond scission.

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