Direct Construction of Acid-Responsive Poly(indolone)s through Multicomponent Tandem Polymerizations

Chunxuan Qi; Chao Zheng; Rongrong Hu; Ben Zhong Tang

doi:10.1021/acsmacrolett.9b00297

Direct Construction of Acid-Responsive Poly(indolone)s through Multicomponent Tandem Polymerizations

ACS Macro Lett. 2019 May 21;8(5):569-575. doi: 10.1021/acsmacrolett.9b00297. Epub 2019 May 2.

Authors

Chunxuan Qi¹, Chao Zheng¹, Rongrong Hu¹, Ben Zhong Tang^{1

2}

Affiliations

¹ State Key Laboratory of Luminescent Materials and Devices, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510641, China.
² Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, China.

PMID: 35619365
DOI: 10.1021/acsmacrolett.9b00297

Abstract

Multicomponent polymerizations (MCPs) as a burgeoning field in polymer chemistry has proved to be a powerful and popular tool for the synthesis of functional polymer materials with diverse and complex structures. To explore the general applicability of MCPs and enrich the product structures of MCPs, multicomponent tandem polymerizations (MCTPs) with great synthetic simplicity and efficiency were pursued. In this work, MCTPs of N-(2-iodophenyl)-3-phenyl-N-tosylpropiolamide, aromatic terminal alkynes, and diamines were explored through combining Sonogashira coupling and Michael addition reaction in a one-pot procedure. The MCTPs could proceed efficiently and conveniently under mild conditions with Pd(PPh₃)₂Cl₂, CuI, and i-Pr₂NEt, affording 12 poly(indolone)s with unique structures and high M_ws (up to 30400 g/mol) in high yields (up to 97%). The poly(indolone)s possess a unique acid-triggered fluorescence "turn-on" response which could realize specific detection of CF₃SO₃H from other inorganic and organic acids through a rapid acid-catalyzed reaction from enamine to ketone.