2-propyl-1-heptyl triflate | 885501-50-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-propyl-1-heptyl triflate
• 英文别名: 2-Propyl-1-heptyl triflate；2-propylheptyl trifluoromethanesulfonate
• CAS: 885501-50-8
• 化学式: C₁₁H₂₁F₃O₃S
• 分子量: 290.347
• InChiKey: ILTZNSJTIGIXCW-UHFFFAOYSA-N

物化性质

• 沸点：
  279.9±35.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-propyl-1-heptyl triflate 、 2-[4-(3,5-dimethyl-pyridin-4-yl)-3,5-dimethyl-phenyl]-malononitrile 以 二氯甲烷 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  超大超极化扭曲 π 电子系统光电发色团：合成、固态和溶液相结构特性、电子结构、线性和非线性光学特性以及计算研究

  摘要：

  该贡献详细介绍了一系列非常规扭曲 pi 电子系统电光 (EO) 发色团的合成和化学/物理表征。这些发色团的晶体学分析显示大的环-环二面角扭曲角（80-89 度）和高度电荷分离的两性离子结构主导基态。溶液中扭曲角的 NOE NMR 测量证实固态扭曲在溶液中基本保持不变。溶液相和固态下的光学、IR 和 NMR 光谱研究进一步证实了固态结构特征在溶液中持续存在。使用几种实验技术研究了这些高极性两性离子的聚集，包括浓度相关的光学和荧光光谱以及脉冲场梯度自旋回波 (PGSE) NMR 光谱与固态数据相结合。这些研究揭示了在浓溶液和固态中形成中心对称聚集体的明确证据，并提供了关于聚集程度的定量信息。溶液相直流电场诱导二次谐波 (EFISH) 测量显示前所未有的超极化（非共振 mubeta 在 1907 nm 处高达 -488,000 x 10(-48) esu）。将这些发色团合并到客体-主机极化聚乙烯苯酚薄膜中提供了非常大的电光系数

  DOI：

  10.1021/ja0674690
• 作为产物：
  描述：

  2-丙基-1-庚醇 在 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 以94.1%的产率得到2-propyl-1-heptyl triflate
  参考文献：
  名称：

  TWISTED PI-ELECTRON SYSTEM CHROMOPHORE COMPOUNDS WITH VERY LARGE MOLECULAR HYPERPOLARIZABILITIES AND RELATED COMPOSITIONS AND DEVICES

  摘要：

  非传统扭曲的π-电子体系电光（EO）色团/化合物，组成和相关器件结构。对几种非限制性色团的晶体学分析显示，例如在溶液相和固态中，存在大的环-环二面角扭转角和高度电荷分离的带电离子结构。

  公开号：

  US20100273919A1

文献信息

• Twisted pi-electron system chromophore compounds with very large molecular hyperpolarizabilities and related compositions and devices
  申请人：Marks J. Tobin

  公开号：US20060237368A1

  公开（公告）日：2006-10-26

  Unconventional twisted π-electron system electro-optic (EO) chromophores/compounds, compositions and related device structures. Crystallographic analysis of several non-limiting chromophores reveals, for instance, large ring-ring dihedral twist angles and a highly charge-separated zwitterionic structure in the ground state, in both solution phase and solid-state.

  非传统扭曲的π电子系统电光（EO）色团/化合物、组成和相关的设备结构。对几种非限制性色团的晶体学分析揭示了，例如大的环-环二面角扭曲角度和高度电荷分离的带电离子结构在基态中，无论是在溶液相还是固态中。
• Twisted Pi-Electron System Chromophore Compounds with Very Large Molecular Hyperpolarizabilities and Related Compositions and Devices
  申请人：Marks Tobin J.

  公开号：US20110278512A1

  公开（公告）日：2011-11-17

  Unconventional twisted π-electron system electro-optic (EO) chromophores/compounds, compositions and related device structures. Crystallographic analysis of several non-limiting chromophores reveals, for instance, large ring-ring dihedral twist angles and a highly charge-separated zwitterionic structure in the ground state, in both solution phase and solid-state.

  非传统的扭曲π电子体系的电光（EO）色团/化合物、组成和相关器件结构。对几种非限制性的色团进行晶体学分析，例如大的环-环二面角扭曲角度以及在溶液相和固态中均表现出高度带电离子结构的基态。
• Twisted π-electron system chromophore compounds with very large molecular hyperpolarizabilities and related compositions and devices
  申请人：Northwestern University

  公开号：US07968016B2

  公开（公告）日：2011-06-28

  Unconventional twisted π-electron system electro-optic (EO) chromophores/compounds, compositions and related device structures. Crystallographic analysis of several non-limiting chromophores reveals, for instance, large ring-ring dihedral twist angles and a highly charge-separated zwitterionic structure in the ground state, in both solution phase and solid-state.

  非传统扭曲π电子体系的电光（EO）色团/化合物、组成和相关器件结构。对几种非限制性的色团进行晶体学分析，例如大环-环二面角扭曲角和高度电荷分离的两性离子结构在基态下，在溶液相和固态下都得到揭示。
• Exceptional Molecular Hyperpolarizabilities in Twisted π-Electron System Chromophores
  作者：Hu Kang、Antonio Facchetti、Peiwang Zhu、Hua Jiang、Yu Yang、Elena Cariati、Stefania Righetto、Renato Ugo、Cristiano Zuccaccia、Alceo Macchioni、Charlotte L. Stern、Zhifu Liu、Seng-Tiong Ho、Tobin J. Marks

  DOI：10.1002/anie.200501581

  日期：2005.12.9
• Ultra-High-Response, Multiply Twisted Electro-optic Chromophores: Influence of π-System Elongation and Interplanar Torsion on Hyperpolarizability
  作者：Yanrong Shi、David Frattarelli、Naoki Watanabe、Antonio Facchetti、Elena Cariati、Stefania Righetto、Elisa Tordin、Cristiano Zuccaccia、Alceo Macchioni、Staci L. Wegener、Charlotte L. Stern、Mark A. Ratner、Tobin J. Marks

  DOI：10.1021/jacs.5b04636

  日期：2015.10.7

  The systematic synthesis, structural, optical spectroscopic, and second-order nonlinear optical (NLO) characterization of a series of donor-acceptor poly-arylene chromophores which have heretofore unachieved pi-extension and substantial twisting from planarity, are reported: specifically, two-ring 2TTMC, dicyano (4-(3,5-dimethyl-1-(2-propylheptyl)-pyridin-1-ium-4-yl)-3-methylphenyl)methanide; three-ring 3TTMC, dicyano (4'-(3,5-dimethyl-1-(2-propylheptyl)pyridin-1-ium-4-yl)-2,2',3',5',6'-pentamethyl[1,1'-biphenyl]-4-yl)methanide; and four-ring 4TTMC, dicyano (4 ''-(3,5-ciimethyl-1- (2-propylheptyl)-pyridin-1-ium-4-yl)-2,2',3 '',6,6'-pentamethyl[1,1':4',1 ''-terphenyl]-4-yl)methanide. Single-crystal X-ray diffraction, DFT-optimized geometries, and B3LYP/INDO-SOS analysis identify three key features underlying the very large NLO response: (1) For ring catenation of three or greater, sterically enforced pi-system twists are only essential near the chromophore donor and acceptor sites to ensure large NLO responses. (2) For synthetic efficiency, deletion of one ortho-methyl group from o,o',o '',o'"-tetramethylbiaryl junctures, only slightly relaxes the biaryl twist angle from 89.6 degrees to similar to 80 degrees. (3) Increased arylene catenation from two to three to four rings (2TTMC -> 3TTMC -> 4TTMC) greatly enhances NLO response, zwitterionic charge localization, and thus the ground-state dipole moment, consistent with the contracted antiparallel solid-state pi-pi stacking distances of 8.665 -> 7.883 -> 7.361 angstrom, respectively. This supports zwitterionic ground states in these chromophores as do significant optical spectroscopic solvatochromic shifts, with aryl-aryl twisting turning on significant intra-subfragment absorption. Computed molecular hyperpolarizabilities (mu beta) approach an unprecedented 900 000 X 10(-48) esu, while estimated chromophore figures of merit, mu beta(vec)/M-w, approach 1500 X 10(-48) esu, 1.5 times larger than the highest known values for twisted chromophores and >33 times larger than that of planar donor-acceptor chromophores.