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

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 Mws (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.

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Field Value
Theme
Author Chunxuan Qi (2573098), Chao Zheng (728465), Rongrong Hu (1423408), Ben Zhong Tang (1272294)
Maintainer
Source https://figshare.com/articles/Direct_Construction_of_Acid-Responsive_Poly_indolone_s_through_Multicomponent_Tandem_Polymerizations/8072213
Source Created 2019-05-02T19:04:13Z
Source Modified 2019-05-02T19:04:13
Language English
Spatial
Source Identifier 10.1021/acsmacrolett.9b00297.s003
Dataset metadata created 16 May 2019, last updated 16 May 2019