121st General Meeting of the KCS

Type Poster Presentation
Area Polymer Chemistry
Room No. Event Hall
Time 4월 20일 (금요일) 11:00~12:30
Code POLY.P-29
Subject Iridium-catalyzed direct C-H amidation polymerization to give fluorescent polysulfonamides
Authors Yoon-Jung Jang, Tae-Lim Choi*
Division of Chemistry, Seoul National University, Korea
Abstract

Direct (hetero)arylation polymerizations(DHAP) have attracted great attention in recent years to synthesize various conjugated polymers such as polythiophenes and polycarbazoles. This polymerization methods are atom-, step-economical because these can reduce the undesired organometallic byproducts and the number of synthetic steps. However, conventional DHAPs are limited to C-C bond formation, and polymerization method for C-N bond formation using C-H activation has remained unexplored to date. Here, we report a Iridium-catalyzed Direct C-H amidation polymerization(DCAP) that enables the synthesis of high-molecular-weight, defect-free polysulfonylamides. We discovered that a reactive directing group, additives, silver salts, and reaction temperature are key factors for efficient DCAP through model study and optimization. This polymerization allowed high-molecular-weight polysulfonylamides with various readily accessible bis-sulfonyl azides. Furthermore, these polymers emit fluorescence with high quantum yields and large stokes shifts due to excited-state intramolecular proton transfer(ESIPT) while these polymers have different structures from conventional fluorescent conjugated polymers. Notably, this research demonstrates a successful atom-, step-economical DCAP showing defect-free, high-molecular-weight fluorescent polysulfonylamides.

E-mail sg99037@snu.ac.kr