2,7-bis(2-bromotetrafluoroethyloxy)naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,7-bis(2-bromotetrafluoroethyloxy)naphthalene
• 英文别名: 2,7-Bis(2-bromo-1,1,2,2-tetrafluoroethoxy)naphthalene；2,7-bis(2-bromo-1,1,2,2-tetrafluoroethoxy)naphthalene
• 化学式: C₁₄H₆Br₂F₈O₂
• 分子量: 517.996
• InChiKey: NNTWLWIRGGYPBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,7-bis(2-bromotetrafluoroethyloxy)naphthalene 在 锌 作用下， 以 乙腈 为溶剂， 反应 29.0h， 以58%的产率得到2,7-bis(trifluorovinyloxy)naphthalene
  参考文献：
  名称：

  Isomer Structure−Optical Property Relationships for Naphthalene-Based Poly(perfluorocyclobutyl ether)s

  摘要：

  Synthesis and characterization of new naphthalene-based PFCB aryl ether polymeric isomers with 1,5-, 1,6-, 2,6-, and 2,7-linkages were described. Monomers of perfluorocyclobutane (PFCB) poly(aryl ether)s, 1,5-, 1,6-, 2,6-, and 2,7-bis(trifluorovinyloxy)naphthalene, were synthesized from dihydroxynaphthalenes in two steps and polymerized by 2 pi + 2 pi step-growth cyclopolymerization. The naphthalene-based PFCB polymers (PFNs) had a relatively high T-g in the range 106-144 degrees C and excellent thermal stability at temperatures up to 400 degrees C. Among PFN polymeric isomers, T-g of the 1,5-linked PFCB polymer (1,5-PFN) was 30-40 degrees C higher than those of the other naphthalene isomers due to its high steric hindrance around the backbone. The refractive index and birefringence of the PFN polymers in the form of spin-coated films were determined. The PFN isomeric polymers showed tunability in refractive index and the bireftingence of the order of 1,5 < 1,6 < 2,6 < 2,7-PFN and 1,5 < 1,6 < 2,7 < 2,6-PFN, respectively. PFN isomers had low birefringences below 0.002 except 2,6-PFN. The lowest value in birefringence was 0.0008 of 1,5-PFN due to its highly kinked structure. Plastic optical fibers of homopolymers, 1,5- and 2,7-PFN, and copolymers, 2,7-co-1,5-PFN and 2,7-PFN-co-6F-PF, were prepared, and optical losses and windows of them were observed. The attenuation loss of PFN polymers was about 0.17-0.27 dB/cm at the wavelength of near-IR optical sources. 1,5-PFN had a lower optical loss than 2,7-PFN. The optical loss of the 2,7-co-1,5-PFN copolymer was effectively reduced compared with that of 2,7-PFN. The lowest optical loss polymer for PFCB POF was 2,7-PFN-co-6F-PF of 0.07 dB/cm at the wavelength of the optical loss window and 0.17 dB/crn at 1300 nm.

  DOI：

  10.1021/ma050500i
• 作为产物：
  描述：

  1,1,2,2-四氟-1,2-二溴乙烷 、 2,7-二羟基萘 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以70%的产率得到2,7-bis(2-bromotetrafluoroethyloxy)naphthalene
  参考文献：
  名称：

  Isomer Structure−Optical Property Relationships for Naphthalene-Based Poly(perfluorocyclobutyl ether)s

  摘要：

  Synthesis and characterization of new naphthalene-based PFCB aryl ether polymeric isomers with 1,5-, 1,6-, 2,6-, and 2,7-linkages were described. Monomers of perfluorocyclobutane (PFCB) poly(aryl ether)s, 1,5-, 1,6-, 2,6-, and 2,7-bis(trifluorovinyloxy)naphthalene, were synthesized from dihydroxynaphthalenes in two steps and polymerized by 2 pi + 2 pi step-growth cyclopolymerization. The naphthalene-based PFCB polymers (PFNs) had a relatively high T-g in the range 106-144 degrees C and excellent thermal stability at temperatures up to 400 degrees C. Among PFN polymeric isomers, T-g of the 1,5-linked PFCB polymer (1,5-PFN) was 30-40 degrees C higher than those of the other naphthalene isomers due to its high steric hindrance around the backbone. The refractive index and birefringence of the PFN polymers in the form of spin-coated films were determined. The PFN isomeric polymers showed tunability in refractive index and the bireftingence of the order of 1,5 < 1,6 < 2,6 < 2,7-PFN and 1,5 < 1,6 < 2,7 < 2,6-PFN, respectively. PFN isomers had low birefringences below 0.002 except 2,6-PFN. The lowest value in birefringence was 0.0008 of 1,5-PFN due to its highly kinked structure. Plastic optical fibers of homopolymers, 1,5- and 2,7-PFN, and copolymers, 2,7-co-1,5-PFN and 2,7-PFN-co-6F-PF, were prepared, and optical losses and windows of them were observed. The attenuation loss of PFN polymers was about 0.17-0.27 dB/cm at the wavelength of near-IR optical sources. 1,5-PFN had a lower optical loss than 2,7-PFN. The optical loss of the 2,7-co-1,5-PFN copolymer was effectively reduced compared with that of 2,7-PFN. The lowest optical loss polymer for PFCB POF was 2,7-PFN-co-6F-PF of 0.07 dB/cm at the wavelength of the optical loss window and 0.17 dB/crn at 1300 nm.

  DOI：

  10.1021/ma050500i

文献信息

• Isomer Structure−Optical Property Relationships for Naphthalene-Based Poly(perfluorocyclobutyl ether)s
  作者：Jieun Ghim、Hwa-Sub Shim、Bu Gon Shin、Jeong-Ho Park、Jin-Teak Hwang、Chaemin Chun、Seong-Hwan Oh、Jang-Joo Kim、Dong-Yu Kim

  DOI：10.1021/ma050500i

  日期：2005.10.1

  Synthesis and characterization of new naphthalene-based PFCB aryl ether polymeric isomers with 1,5-, 1,6-, 2,6-, and 2,7-linkages were described. Monomers of perfluorocyclobutane (PFCB) poly(aryl ether)s, 1,5-, 1,6-, 2,6-, and 2,7-bis(trifluorovinyloxy)naphthalene, were synthesized from dihydroxynaphthalenes in two steps and polymerized by 2 pi + 2 pi step-growth cyclopolymerization. The naphthalene-based PFCB polymers (PFNs) had a relatively high T-g in the range 106-144 degrees C and excellent thermal stability at temperatures up to 400 degrees C. Among PFN polymeric isomers, T-g of the 1,5-linked PFCB polymer (1,5-PFN) was 30-40 degrees C higher than those of the other naphthalene isomers due to its high steric hindrance around the backbone. The refractive index and birefringence of the PFN polymers in the form of spin-coated films were determined. The PFN isomeric polymers showed tunability in refractive index and the bireftingence of the order of 1,5 < 1,6 < 2,6 < 2,7-PFN and 1,5 < 1,6 < 2,7 < 2,6-PFN, respectively. PFN isomers had low birefringences below 0.002 except 2,6-PFN. The lowest value in birefringence was 0.0008 of 1,5-PFN due to its highly kinked structure. Plastic optical fibers of homopolymers, 1,5- and 2,7-PFN, and copolymers, 2,7-co-1,5-PFN and 2,7-PFN-co-6F-PF, were prepared, and optical losses and windows of them were observed. The attenuation loss of PFN polymers was about 0.17-0.27 dB/cm at the wavelength of near-IR optical sources. 1,5-PFN had a lower optical loss than 2,7-PFN. The optical loss of the 2,7-co-1,5-PFN copolymer was effectively reduced compared with that of 2,7-PFN. The lowest optical loss polymer for PFCB POF was 2,7-PFN-co-6F-PF of 0.07 dB/cm at the wavelength of the optical loss window and 0.17 dB/crn at 1300 nm.