6,7-bis(thiophenyl)-2,3-dicyanonaphthalene | 126750-55-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6,7-bis(thiophenyl)-2,3-dicyanonaphthalene
• 英文别名: 6,7-bis-(thiophenyl)naphthalonitrile；6,7-bis-(phenylthio)naphthalene-2,3-dicarbonitrile；6,7-Bis(phenylsulfanyl)naphthalene-2,3-dicarbonitrile；6,7-bis(phenylsulfanyl)naphthalene-2,3-dicarbonitrile
• CAS: 126750-55-8
• 化学式: C₂₄H₁₄N₂S₂
• 分子量: 394.521
• InChiKey: FSEHUQMJWYTNRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cerium(III) acetylacetonate hydrate 、 6,7-bis(thiophenyl)-2,3-dicyanonaphthalene 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 辛醇 为溶剂， 反应 18.0h， 以5.6%的产率得到
  参考文献：
  名称：

  Infra-red spectroscopic characteristics of naphthalocyanine in bis(naphthalocyaninato) rare earth complexes peripherally substituted with thiophenyl derivatives

  摘要：

  The infra-red (IR) spectroscopic data for a series of eleven rare earth double-deckers M-III[Nc(SPh)(8)](2) (M = Y, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho and Er) have been collected and systematically investigated. For M-III[Nc(SPh)(8)](2), typical IR marker bands for the naphthalocyanine anion radical [Nc(SPh)(8)](.-) were observed at 1317-1325 cm(-1) as the most intense absorption bands, which can be attributed to the pyrrole stretching. As for Ce[Nc(SPh)(8)](2), the typical IR marker band was also observed at 1317 cm-1, which shows that the cerium complex exists as the form of Ce-III[Nc(SPh)(8)](2)(-)[Nc(SPh)(8)](.-). In addition, both the Q-bands of electronic absorption spectra and the typical IR absorption bands of naphthalocyanine radical anion [Nc(SPh)(8)](.-) move to the high energy as the decrease of rare earth metal ionic radius. These facts suggest that the pi-pi electron interaction in these double-deckers becomes stronger along with the lanthanide contraction. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.12.079
• 作为产物：
  描述：

  2,3-二溴-6,7-二氰基萘 、 sodium thiophenolate 以20%的产率得到6,7-bis(thiophenyl)-2,3-dicyanonaphthalene
  参考文献：
  名称：

  Kitahara, Kiyoshi; Asano, Toyofumi; Kayama, Susumu, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 67, # 1-4, p. 373 - 376

  摘要：

  DOI：

文献信息

• New mixed rare earth double-decker complexes with octyloxynaphthyl-porphyrinato and phenylthio-naphthalocyaninato ligands – preparation and spectroscopic characterization
  作者：Xiaobo Li、Yajun Mao、Fanli Lu

  DOI：10.1080/00958972.2015.1102899

  日期：2015.12.2

  Eight new (porphyrinato)(naphthalocyaninato) rare earth(III) double-decker complexes MIII(TONPP)[Nc(PhS)8] [M = La, Pr, Nd, Sm, Eu, Gd, Tb, and Dy; TONPP = 5,10,15,20-tetrakis(4-octyloxynaphthyl) porphyrin; Nc(PhS)8 = 3,4,12,13,21,22,30,31-octa(phenylthio)-2,3-naphthalocyanine] have been prepared and characterized by spectroscopic methods. The UV–vis absorption spectra depend on the central rare earth

  八种新型 (porphyrinato)(naphthalocyaninato) 稀土 (III) 双层复合物 MIII(TONPP)[Nc(PhS)8] [M = La、Pr、Nd、Sm、Eu、Gd、Tb 和 Dy；TONPP = 5,10,15,20-四（4-辛氧基萘基）卟啉；Nc(PhS)8 = 3,4,12,13,21,22,30,31-octa(phenylthio)-2,3-naphthalocyanine] 已通过光谱方法制备和表征。UV-vis 吸收光谱取决于中心稀土离子大小，表明所有跃迁都涉及分子轨道，卟啉和萘酞菁配体都有贡献。对这些双层化合物的红外光谱和拉曼光谱进行了系统研究，表明这些混合双层化合物中的电子空穴主要位于萘酞菁环上。它们的夹心性质还通过 MS、EA 和 1H NMR 技术进行了表征。
• Synthetic studies of substituted 2,3-naphthalocyanines
  作者：Yee-On Yeung、Roger C.W. Liu、Wing-Fong Law、Pik-Ling Lau、Jianzhuang Jiang、Dennis K.P. Ng

  DOI：10.1016/s0040-4020(97)00601-7

  日期：1997.7

  A series of di- and tetra-substituted 2,3-dicyanonaphthalenes were prepared which were converted into the respective 2,3-naphthalocyaninato zinc complexes. The synthetic pathways to and the spectroscopic properties of these novel compounds are described. (C) 1997 Elsevier Science Ltd.
• Kitahara, Kiyoshi; Asano, Toyofumi; Kayama, Susumu, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 67, # 1-4, p. 373 - 376
  作者：Kitahara, Kiyoshi、Asano, Toyofumi、Kayama, Susumu、Tokita, Sumio、Nishi, Hisao

  DOI：——

  日期：——
• Infra-red spectroscopic characteristics of naphthalocyanine in bis(naphthalocyaninato) rare earth complexes peripherally substituted with thiophenyl derivatives
  作者：Xiaobo Li、Yajun Mao、Chi Xiao、Fanli Lu

  DOI：10.1016/j.saa.2014.12.079

  日期：2015.4

  The infra-red (IR) spectroscopic data for a series of eleven rare earth double-deckers M-III[Nc(SPh)(8)](2) (M = Y, Ce, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho and Er) have been collected and systematically investigated. For M-III[Nc(SPh)(8)](2), typical IR marker bands for the naphthalocyanine anion radical [Nc(SPh)(8)](.-) were observed at 1317-1325 cm(-1) as the most intense absorption bands, which can be attributed to the pyrrole stretching. As for Ce[Nc(SPh)(8)](2), the typical IR marker band was also observed at 1317 cm-1, which shows that the cerium complex exists as the form of Ce-III[Nc(SPh)(8)](2)(-)[Nc(SPh)(8)](.-). In addition, both the Q-bands of electronic absorption spectra and the typical IR absorption bands of naphthalocyanine radical anion [Nc(SPh)(8)](.-) move to the high energy as the decrease of rare earth metal ionic radius. These facts suggest that the pi-pi electron interaction in these double-deckers becomes stronger along with the lanthanide contraction. (C) 2014 Elsevier B.V. All rights reserved.