N-[4-(9-phenanthrenyl)butyl-2-(2-phenyl-1-thioxo)thio]-propanamide | 918155-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N-[4-(9-phenanthrenyl)butyl-2-(2-phenyl-1-thioxo)thio]-propanamide
• 英文别名: PBTP；[1-Oxo-1-(4-phenanthren-9-ylbutylamino)propan-2-yl] benzenecarbodithioate；[1-oxo-1-(4-phenanthren-9-ylbutylamino)propan-2-yl] benzenecarbodithioate
• CAS: 918155-49-4
• 化学式: C₂₈H₂₇NOS₂
• 分子量: 457.66
• InChiKey: PVTXGDZLQLBWQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  succinimido-2-[[2-phenyl-1-thioxo]thio]propanoate 、 4-(9-phenanthrenyl)butyl amine hydrochloride 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以65%的产率得到N-[4-(9-phenanthrenyl)butyl-2-(2-phenyl-1-thioxo)thio]-propanamide
  参考文献：
  名称：

  RAFT polymerization and self-assembly of thermoresponsive poly(N-decylacrylamide-b-N,N-diethylacrylamide) block copolymers bearing a phenanthrene fluorescent α-end group

  摘要：

  Phenanthrene alpha-end-labeled poly(N-decylacrylamide-b-N,N-diethylacrylamide) (PDcA(n)-b-PDEA(m)) block copolymers consisting in a highly hydrophobic block (n = 11) and a thermo responsive block with variable length (79 <= m <= 468) were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. A new phenanthrene-labeled chain transfer agent (CTA) was synthesized and used to control the RAFT polymerization of a hydrophobic acrylamide derivative, N-decylacrylamide (DcA). This first block was further used as macroCTA to polymerize N,N-diethylacrylamide (DEA) in order to prepare diblock copolymers with the same hydrophobic block of PDcA (number average molecular weight: M-n = 2720 g mol(-1), polydispersity index: M-w/M-n = 1.13) and various PDEA blocks of several lengths M-n = 10,000-60,000 g mol(-1)) with a very high blocking efficiency. The resulting copolymers self-assemble in water forming thermoresponsive micelles. The critical micelle concentration (CMC) was determined using Forster resonance energy transfer (FRET) between phenanthrene linked at the end of the PDcA block and anthracene added to the solution at a low concentration (10(-5) M), based on the fact that energy transfer only occurs when phenanthrene and anthracene are located in the core of the micelle. The CMC (similar to 2 mu M) was obtained at the polymer concentration where the anthracene fluorescence intensity starts to increase. The size of the polymer micelles decreases with temperature increase around the lower critical solution temperature of PDEA in water (LCST similar to 32 degrees C) owing to the thermoresponsiveness of the PDEA shell. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2009.11.055

文献信息

• RAFT polymerization and self-assembly of thermoresponsive poly(N-decylacrylamide-b-N,N-diethylacrylamide) block copolymers bearing a phenanthrene fluorescent α-end group
  作者：Telmo J.V. Prazeres、Mariana Beija、Marie-Thérèse Charreyre、José Paulo S. Farinha、José M.G. Martinho

  DOI：10.1016/j.polymer.2009.11.055

  日期：2010.1

  Phenanthrene alpha-end-labeled poly(N-decylacrylamide-b-N,N-diethylacrylamide) (PDcA(n)-b-PDEA(m)) block copolymers consisting in a highly hydrophobic block (n = 11) and a thermo responsive block with variable length (79 <= m <= 468) were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. A new phenanthrene-labeled chain transfer agent (CTA) was synthesized and used to control the RAFT polymerization of a hydrophobic acrylamide derivative, N-decylacrylamide (DcA). This first block was further used as macroCTA to polymerize N,N-diethylacrylamide (DEA) in order to prepare diblock copolymers with the same hydrophobic block of PDcA (number average molecular weight: M-n = 2720 g mol(-1), polydispersity index: M-w/M-n = 1.13) and various PDEA blocks of several lengths M-n = 10,000-60,000 g mol(-1)) with a very high blocking efficiency. The resulting copolymers self-assemble in water forming thermoresponsive micelles. The critical micelle concentration (CMC) was determined using Forster resonance energy transfer (FRET) between phenanthrene linked at the end of the PDcA block and anthracene added to the solution at a low concentration (10(-5) M), based on the fact that energy transfer only occurs when phenanthrene and anthracene are located in the core of the micelle. The CMC (similar to 2 mu M) was obtained at the polymer concentration where the anthracene fluorescence intensity starts to increase. The size of the polymer micelles decreases with temperature increase around the lower critical solution temperature of PDEA in water (LCST similar to 32 degrees C) owing to the thermoresponsiveness of the PDEA shell. (C) 2009 Elsevier Ltd. All rights reserved.