Aminobisphosphonate Polymers via RAFT and a Multicomponent Kabachnik-Fields Reaction

被引：40
|
作者：
Bachler, Patricia R. [1 ]
Schulz, Michael D. [1 ]
Sparks, Chelsea A. [1 ]
Wagener, Kenneth B. [1 ]
Sumerlin, Brent S. [1 ]
机构：
[1] Univ Florida, Dept Chem, George & Josephine Butler Polymer Res Lab, Ctr Macromol Sci & Engn, Gainesville, FL 32611 USA
来源：
MACROMOLECULAR RAPID COMMUNICATIONS | 2015年 / 36卷 / 09期
基金：
美国国家科学基金会;
关键词：
aminobisphosphonate; Kabachnik-Fields; Moedritzer-Irani; multicomponent reactions; postpolymerization reactions; reversible addition-fragmentation chain transfer; PHOSPHORUS-CONTAINING POLYMERS; ONE-POT SYNTHESIS; IN-VITRO; RADICAL POLYMERIZATION; BISPHOSPHONATES; CHEMISTRY; POLYPHOSPHATES; OPPORTUNITY; POLYAMIDES; COPOLYMERS;
D O I：
10.1002/marc.201500060
中图分类号：
O63 [高分子化学（高聚物）];
学科分类号：
070305 ; 080501 ; 081704 ;
摘要：
Polyacrylamides containing pendant aminobisphosphonate groups are synthesized via reversible addition-fragmentation chain transfer (RAFT) polymerization and a multicomponent postpolymerization functionalization reaction. A Moedritzer-Irani reaction installs the phosphonic acid groups on well-defined, RAFT-generated polymers bearing a pendant amine. An alternate route to the same materials is developed utilizing a three-component Kabachnik-Fields reaction and subsequent dealkylation. Kinetics of the RAFT polymerization of the polymer precursor are studied. Successful functionalization is demonstrated by NMR and FTIR spectroscopy and elemental analysis of the final polymers.
引用
收藏
页码：828 / 833
页数：6
相关论文
共 50 条
  • [41] Hyperbranched Bisphosphonate-Functional Polymers via Self-Condensing Vinyl Polymerization and Postpolymerization Multicomponent Reactions
    Calvo, Patricia R.
    Sparks, Chelsea A.
    Hochberg, Justin
    Wagener, Kenneth B.
    Sumerlin, Brent S.
    MACROMOLECULAR RAPID COMMUNICATIONS, 2021, 42 (06)
  • [42] Three component Kabachnik-Fields condensation leading to substituted aminomethane-P-hydroxymethylphosphonic acids as a tool for screening of bacterial urease inhibitors
    Vassiliou, Stamatia
    Grabowiecka, Agnieszka
    Kosikowska, Paulina
    Berlicki, Lukasz
    ARKIVOC, 2012, : 33 - 43
  • [43] Versatile Routes to Functional RAFT Chain Transfer Agents through the Passerini Multicomponent Reaction
    Pearce, Amanda K.
    Travanut, Alessandra
    Couturaud, Benoit
    Taresco, Vincenzo
    Howdle, Steven M.
    Alexander, Morgan R.
    Alexander, Cameron
    ACS MACRO LETTERS, 2017, 6 (07): : 781 - 785
  • [44] Synthesis of amphiphilic fluorescent polymers via a one-pot combination of multicomponent Hantzsch reaction and RAFT polymerization and their cell imaging applications
    Huang, Zengfang
    Chen, Qiaomei
    Wan, Qing
    Wang, Ke
    Yuan, Jinying
    Zhang, Xiaoyong
    Tao, Lei
    Wei, Yen
    POLYMER CHEMISTRY, 2017, 8 (33) : 4805 - 4810
  • [45] A Critical Overview of the Kabachnik-Fields Reactions Utilizing Trialkyl Phosphites in Water as the Reaction Medium: A Study of the Benzaldehyde-Benzylamine Triethyl Phosphite/Diethyl Phosphite Models
    Keglevich, Gyoergy
    Balint, Erika
    Kangyal, Reka
    Balint, Maria
    Milen, Matyas
    HETEROATOM CHEMISTRY, 2014, 25 (04) : 282 - 289
  • [46] The Synthesis of N,N-Bis(dialkoxyphosphinoylmethyl)- and N,N-Bis(diphenylphosphinoylmethyl) glycine Esters by the Microwave-Assisted Double Kabachnik-Fields Reaction
    Balint, Erika
    Fazekas, Eszter
    Drahos, Laszlo
    Keglevich, Gyoergy
    HETEROATOM CHEMISTRY, 2013, 24 (06) : 510 - 515
  • [47] New Possibilities of the Kabachnik-Fields and Pudovik Reactions in the Phthalocyanine-Catalyzed Syntheses of -Aminophosphonic and -Aminophosphinic Acid Derivatives
    Shuvalov, M. V.
    Maklakova, S. Yu.
    Rudakova, E. V.
    Kovaleva, N. V.
    Makhaeva, G. F.
    Podrugina, T. A.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (09) : 1761 - 1775
  • [48] Magnetic BaFe12O19/Al2O3: An Efficient Heterogeneous Lewis Acid Catalyst for the Synthesis of α-Aminophosphonates (Kabachnik-Fields Reaction)
    Piri, Tayebeh
    Peymanfar, Reza
    Javanshir, Shahrzad
    Amirnejat, Sara
    CATALYSIS LETTERS, 2019, 149 (12) : 3384 - 3394
  • [49] Synthetic utility of Kabachnik-Fields reaction: a convenient one-pot three-component synthesis of N-phenyl isoquinolone-1-phosphonates
    Borse, Amulrao U.
    Patil, Nilesh L.
    Patil, Mahesh N.
    Mali, Raghao S.
    TETRAHEDRON LETTERS, 2012, 53 (51) : 6940 - 6942
  • [50] Fluorescent protein-reactive polymers via one-pot combination of the Ugi reaction and RAFT polymerization
    Wu, Haibo
    Yang, Bin
    Zhao, Yuan
    Wei, Yen
    Wang, Zhiming
    Wang, Xing
    Tao, Lei
    POLYMER CHEMISTRY, 2016, 7 (30) : 4867 - 4872
12345