Efficient Conversion of Inert Nitriles to Multifunctional Poly(5-amino-1,2,3-triazole)s via Regioselective Click Polymerization with Azide Monomers under Ambient Conditions

Jia Wang; Tian Tian; Rongyuan Zhang; Mingzhao Li; Jie Chen; Anjun Qin; Ben Zhong Tang

doi:10.1021/jacs.3c12588

Efficient Conversion of Inert Nitriles to Multifunctional Poly(5-amino-1,2,3-triazole)s via Regioselective Click Polymerization with Azide Monomers under Ambient Conditions

J Am Chem Soc. 2024 Mar 13;146(10):6652-6664. doi: 10.1021/jacs.3c12588. Epub 2024 Feb 28.

Authors

Jia Wang^{1

2

3}, Tian Tian^{1

2}, Rongyuan Zhang⁴, Mingzhao Li^{1

2}, Jie Chen^{1

2}, Anjun Qin^{1

2}, Ben Zhong Tang^{2

4

5}

Affiliations

¹ State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, South China University of Technology, Guangzhou 510640, China.
² Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, China.
³ Songshan Lake Materials Laboratory, Dongguan 523808, China.
⁴ School of Science and Engineering, Shenzhen Institute of Aggregate Science and Technology, The Chinese University of Hong Kong (CUHK), Shenzhen, Guangdong 518172, China.
⁵ Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, The Hong Kong University of Science and Technology, Kowloon, Hong Kong 999077, China.

PMID: 38419303
DOI: 10.1021/jacs.3c12588

Abstract

Nitrile compounds are abundant, stable, cheap, and readily available natural and chemical industrial sources. However, the efficient conversion of nitrile monomers to functional polymers is mostly limited due to their inert reactivity, and developing efficient polymerizations based on nitrile monomers under very mild conditions is still a big challenge. In this work, a facile and powerful base-catalyzed acetonitrile-azide click polymerization was successfully established under ambient conditions. This polymerization also enjoys the merits of short reaction time (15 min), 100% atom economy, transition-metal-free catalyst system, and regioselectivity. A series of poly(5-amino-1,2,3-triazole)s (PATAs) with high weight-average molecular weights (M_w, up to 204,000) were produced in excellent yields (up to 99%). The PATAs containing tetraphenylethene (TPE) moieties exhibit unique aggregation-induced emission (AIE) characteristics, which could be used to sensitively detect Fe(III) ions with a low limit of detection (1.205 × 10^-7 M) and to specifically image lysosomes of living cells. Notably, PATAs could be facilely post-modified due to their containing primary amino groups in the polymer chains even through a one-pot tandem reaction. Thus, this work not only establishes a new powerful click polymerization to convert stable nitriles but also generates a series of PATAs with versatile properties for diverse applications.