3,5-bis(11-ferrocenylundecyloxy)benzoic acid | 1365259-36-4

• 英文名称: 3,5-bis(11-ferrocenylundecyloxy)benzoic acid
• 英文别名: Fc2COOH
• CAS: 1365259-36-4
• 化学式: C₄₉H₆₆Fe₂O₄
• 分子量: 830.755
• InChiKey: VRSAVHQHDUICCC-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  poly(ethylene glycol) monomethyl ether 、 3,5-bis(11-ferrocenylundecyloxy)benzoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以49.2%的产率得到PEO45-b-Fc2
  参考文献：
  名称：

  Novel Ferrocenyl-Terminated Linear–Dendritic Amphiphilic Block Copolymers: Synthesis, Redox-Controlled Reversible Self-Assembly, and Oxidation-Controlled Release

  摘要：

  Novel linear dendritic amphiphilic block copolymers with hydrophilic poly(ethylene glycol) (PEG) block and hydrophobic Percec-type dendrons containing ferrocenyl terminals were synthesized by the esterification reaction of poly(ethylene glycol) methyl ether with ferrocenyl-terminated alkyl-substituted benzoic acid dendrons. On the basis of the results that the critical aggregation concentration (CAC(ox)) of the oxidation state polymer is much higher than CAC(red) of the corresponding reduction state, these polymers can reversibly self-assemble into various aggregates, such as spherical, wormlike micelles, and vesicles, and also disassemble into irregular fragments in aqueous solution by redox reaction when changing the polymer concentrations. Copolymer PEG(45)-b-Fc(3) (3) with 3,4,5-tris(11-ferrocenylundecyloxy) benzoic acid (2) can self-assemble into nanoscale wormlike micelles when the polymer concentration in aqueous solution is above its CAC(ox). These wormlike micelles can be transformed into nanosized vesicles by Fe-2(SO4)(3) and regained by vitamin C. Interestingly, copolymer PEG(45)-b-Fc(2) (5) with 3,5-bis(11-ferrocenylundecyloxy) benzoic acid (4) can reversibly self-assemble into spherical micelles with two different sizes by redox reaction above the CAC(ox), indicating that the terminal hydrophobic tail number of dendrons plays a key role in determining the self-assembled structures. Furthermore, rhodamine 6G (R6G)-loaded polymer aggregates have been successfully used for the oxidation-controlled release of loaded molecules, and the release rate can be mediated by the concentrations of oxidant and copolymers. The results provide an effective approach to the reversible self-assembly of linear dendritic amphiphilic block copolymers and also promise the potential of these novel redox-responsive amphiphilic block copolymers in drug delivery systems, catalyst supports, and other research fields.

  DOI：

  10.1021/la501652r