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Nucleophilic Substitution Polymerization‐Induced Emission of 1,3‐Dicarbonyl Compounds as a Versatile Approach for Aggregation‐Induced Emission Type Non‐Traditional Intrinsic Luminescence
Ist Teil von
Chinese journal of chemistry, 2023-07, Vol.41 (14), p.1705-1712
Ort / Verlag
Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA
Erscheinungsjahr
2023
Quelle
Wiley-Blackwell Journals
Beschreibungen/Notizen
Comprehensive Summary
Nucleophilic substitution reaction and 1,3‐dicarbonyl compounds play significant roles in organic chemistry, and non‐traditional intrinsic luminescence (NTIL) has become an emerging research area. Here, we demonstrate the successful nucleophilic substitution polymerization of 1,3‐dicarbonyl compounds, including acetylacetone, 3,5‐heptanedione, methyl acetoacetate, cyclopentane‐1,3‐dione, 1,3‐indandione, 1‐phenyl‐1,3‐butanedione and dibenzoylmethane, where reactive hydrogens at α position of 1,3‐dicarbonyl compounds are involved. Through this base catalyzed nucleophilic substitution polycondensation between 1,3‐dicarbonyl compounds and α,α’‐dibromo xylene, a series of nonconjugated poly(1,3‐dicarbonyl)s have been successfully prepared with high yield (up to >99%) under mild conditions. Investigations reveal that this nucleophilic substitution polycondensation exhibits self‐accelerating effect and flexible stoichiometry characteristics, which exhibits advantages over traditional polycondensation methods. This polymerization also exhibits intriguing polymerization‐induced emission (PIE) characteristics, where nonconjugated poly(1,3‐dicarbonyl)s exhibit intriguing chemical structure dependent aggregation‐induced emission (AIE) type NTIL. This work therefore expands the monomer, method, chemical structure and property libraries of polymer chemistry, which may cause inspirations to polymerization methodology, PIE, AIE and NTIL.
Nucleophilic substitution reaction and 1,3‐dicarbonyl compounds have become an emerging research area in organic chemistry. Here, we demonstrate the successful nucleophilic substitution polymerization of 1,3‐dicarbonyl compounds, where non‐traditional intrinsic luminescent poly(1,3‐dicarbonyl)s have been successfully prepared with high yield (up to >99%) under mild conditions.