2,5-Bis[4-(azidomethyl)phenyl]-3,4-diphenylthiophene | 1314963-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,5-Bis[4-(azidomethyl)phenyl]-3,4-diphenylthiophene
• 英文别名: 2,5-bis[4-(azidomethyl)phenyl]-3,4-diphenylthiophene
• CAS: 1314963-78-4
• 化学式: C₃₀H₂₂N₆S
• 分子量: 498.611
• InChiKey: RAAYHLYQHZBUEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以92%的产率得到2,5-Bis[4-(azidomethyl)phenyl]-3,4-diphenylthiophene
  参考文献：
  名称：

  Tetraphenylthiophene-Functionalized Poly(N-isopropylacrylamide): Probing LCST with Aggregation-Induced Emission

  摘要：

  A hydrophobic tetraphenylthiophene (TP) center with novel aggregation-induced emission (AIR) property was chemically linked to two poly(N-isoprppylacrylamide) (PNIPAM) chains to obtain thermoresponsive polymers to study the relationships between the lower critical solution transitions (LCSTs) and the ALE-operative fluorenscence (FL) emission. Three ethynyl-terminated PNIPAMs with different molecular weights were synthesized via controlled atom transfer radical polymerization (ATRP) using ethynyl-functionalized initiator. The PNIPAMs were then coupled with diazide-funtionalized TP (TPN3) via click reaction to obtain the desired TP-embedded polymers of Px (x = 1, 2, and 3). All three polymers show AIE-property from their solution fluorescence behavior in THF/hexane mixtures. In the aqueous solution, the TP-center served as a fluorogenic probe that reveals the LCSTs of polymers and its relation to the degree of TP labeling in terms of polymer concentration. The thermoresponsiveness of Px was demonstrated by the complete emission quench when heated at temperatures above LCST. Dissociation of the TP aggregates above LCST is responsible for the emission quench, which was evaluated through the uses of transmittance measurement, dynamic light scattering, and H-1 NMR spectra.

  DOI：

  10.1021/ma201089j

文献信息

• Tetraphenylthiophene-Functionalized Poly(<i>N</i>-isopropylacrylamide): Probing LCST with Aggregation-Induced Emission
  作者：Chung-Tin Lai、Rong-Hong Chien、Shiao-Wei Kuo、Jin-Long Hong

  DOI：10.1021/ma201089j

  日期：2011.8.23

  A hydrophobic tetraphenylthiophene (TP) center with novel aggregation-induced emission (AIR) property was chemically linked to two poly(N-isoprppylacrylamide) (PNIPAM) chains to obtain thermoresponsive polymers to study the relationships between the lower critical solution transitions (LCSTs) and the ALE-operative fluorenscence (FL) emission. Three ethynyl-terminated PNIPAMs with different molecular weights were synthesized via controlled atom transfer radical polymerization (ATRP) using ethynyl-functionalized initiator. The PNIPAMs were then coupled with diazide-funtionalized TP (TPN3) via click reaction to obtain the desired TP-embedded polymers of Px (x = 1, 2, and 3). All three polymers show AIE-property from their solution fluorescence behavior in THF/hexane mixtures. In the aqueous solution, the TP-center served as a fluorogenic probe that reveals the LCSTs of polymers and its relation to the degree of TP labeling in terms of polymer concentration. The thermoresponsiveness of Px was demonstrated by the complete emission quench when heated at temperatures above LCST. Dissociation of the TP aggregates above LCST is responsible for the emission quench, which was evaluated through the uses of transmittance measurement, dynamic light scattering, and H-1 NMR spectra.