Ethynyl-Directed Dual C(sp3)-H Activation Polymerization to Construct Regio- and Stereoregular C(sp3)-C(sp3) Bond Polymers

被引:3
|
作者
Wang, Jia [3 ]
Li, Mingzhao [1 ]
Xu, Liguo [2 ]
Huang, Die [1 ]
Qin, Anjun [1 ]
Wang, Xin [3 ]
机构
[1] South China Univ Technol, Ctr Aggregat Induced Emiss, State Key Lab Luminescent Mat & Devices, AIE Inst,Guangdong Prov Key Lab Luminescence Mol,A, Guangzhou 510640, Peoples R China
[2] Shunde Polytech, Coll Light Chem Ind & Mat Engn, Foshan 528333, Peoples R China
[3] Songshan Lake Mat Lab, Dongguan 523808, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
C-H ACTIVATION; INTERNAL DIYNES; PRONUCLEOPHILES; ALLYLATION; ALKYNES; DIOLS;
D O I
10.1021/acs.macromol.3c02132
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The establishment of facile, efficient, and precise synthetic approaches to selectively convert stable C-H bonds to functional polymers has great significance in both chemistry and material science especially by C(sp(3))-H activation. Here, an efficient dual C(sp(3))-H activation polymerization of alkynes and activated methylenes catalyzed by Pd(PPh3)(4)/benzoic acid was successfully established with a 100% atom economy and excellent regio- and stereoselectivity. A series of high-weight-average molecular-weight (M-w of approximately 66,500) poly(aryl butene)s (PABs) with a sole E configuration were generated in remarkable yields (approximately 99%). PABs exhibit good thermal stability, excellent solubility, and great film-forming ability. In addition, the thin PAB films display high refractive indices (RI) of up to 1.7126 at 589 nm. Because this polymerization has a strong functional group tolerance, luminophores can be readily constructed into the main chain to empower PABs with efficient and multicolored luminescence in various states. Notably, PABs containing a tetraphenylethene (TPE) moiety feature unique aggregation-induced emission (AIE) peculiarities, which could specifically and sensitively detect Fe(III) ions with a low limit of detection (LOD) of 1.585 x 10(-6) M.
引用
收藏
页码:122 / 131
页数:10
相关论文
共 50 条
  • [21] Iron-Catalyzed C(sp3)-C(sp3) Bond Formation through C(sp3)-H Functionalization: A Cross-Coupling Reaction of Alcohols with Alkenes
    Zhang, Shu-Yu
    Tu, Yong-Qiang
    Fan, Chun-An
    Zhang, Fu-Min
    Shi, Lei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (46) : 8761 - 8765
  • [22] Unusual C-H Bond Activation and C(sp3)-C(sp3) Bond Formation at an Fe(II) Bis(amide) Carbene Complex
    Wong, Anthony
    Guevara, Kevin
    Wu, Guang
    Menard, Gabriel
    ORGANOMETALLICS, 2020, 39 (01) : 116 - 122
  • [23] Iron-Catalyzed C(sp3)-C(sp3) Coupling to Construct Quaternary Carbon Centers
    Zhang, Qiao
    Liu, Xiang-Yu
    Zhang, Yan-Dong
    Huang, Ming-Yao
    Zhang, Xin-Yu
    Zhu, Shou-Fei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (08) : 5051 - 5055
  • [24] C(sp3)-C(sp3) coupling polymerization of alkyl dibromides for preparation of polymers with precisely located phenyl pendants
    Zou, Lei
    Long, Meilin
    Zhou, Houbo
    Zhu, Wen
    Zhang, Ke
    Chen, Yongming
    Xi, Fu
    POLYMER, 2015, 64 : 196 - 201
  • [25] Cobalt-catalysed enantioselective C(sp3)–C(sp3) coupling
    Yan Li
    Wan Nie
    Zhe Chang
    Jia-Wang Wang
    Xi Lu
    Yao Fu
    Nature Catalysis, 2021, 4 : 901 - 911
  • [26] Practical Catalytic Cleavage of C(sp3)-C(sp3) Bonds in Amines
    Li, Wu
    Liu, Weiping
    Leonard, David K.
    Rabeah, Jabor
    Junge, Kathrin
    Brueckner, Angelika
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (31) : 10693 - 10697
  • [27] Cobalt-catalysed enantioselective C(sp3)-C(sp3) coupling
    Li, Yan
    Nie, Wan
    Chang, Zhe
    Wang, Jia-Wang
    Lu, Xi
    Fu, Yao
    NATURE CATALYSIS, 2021, 4 (10) : 901 - 911
  • [28] Photoredox Catalyzed C(sp3)-C(sp3) Coupling of α-Bromoesters and Triethylamine
    Guerra, Allie W.
    Pierce, Joshua G.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (01): : 810 - 814
  • [29] Palladium-Catalyzed Domino Mizoroki-Heck/Intermolecular C(sp3)-H Activation Sequence: An Approach to the Formation of C(sp3)-C(sp3) Bonds
    Wang, Wei
    Zhou, Rong
    Jiang, Zhi-Jie
    Wang, Xin
    Fu, Hai-Yan
    Zheng, Xue-Li
    Chen, Hua
    Li, Rui-Xiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (12) : 2579 - 2584
  • [30] CatalyticdiastereoselectiveandenantioconvergentC(sp3)–C(sp3)cross-couplingofracemicpartners
    Ai-E Wang
    Pei-Qiang Huang
    Science China(Chemistry), 2020, 63 (07) : 871 - 872