Nucleophilic Substitution Polymerization-Induced Emission of 1,3-Dicarbonyl Compounds as a Versatile Approach for Aggregation-Induced Emission Type Non-Traditional Intrinsic Luminescence†
Yu-Jiao Chen
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
Search for more papers by this authorMeng-Qin Pu
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian, 350007 China
Search for more papers by this authorLiang-Tao Wu
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
Search for more papers by this authorCorresponding Author
Xiao-Li Sun
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Wen-Ming Wan
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian, 350007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorYu-Jiao Chen
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
Search for more papers by this authorMeng-Qin Pu
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian, 350007 China
Search for more papers by this authorLiang-Tao Wu
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
Search for more papers by this authorCorresponding Author
Xiao-Li Sun
College of Environment and Resources, Engineering Research Center of Polymer Green Recycling of Ministry of Education, Fujian Key Laboratory of Pollution Control &Resource Reuse, Fujian Normal University, Fuzhou, Fujian, 350007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Wen-Ming Wan
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, 155 Yangqiao Road West, Fuzhou, Fujian, 350002 China
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou, Fujian, 350007 China
E-mail: [email protected]; [email protected]Search for more papers by this authorDedicated to the Special Issue of Emerging Themes in Polymer Science.
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.
Supporting Information
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Appendix S1: Supporting Information |
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