1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene
• 英文别名: 4,4,5,5,6,6-Hexafluoro-5,6,9a,9b-tetrahydro-9a,9b-dimethyl-4H-indeno[5,4-b:6,7-b']dithiophene-2,8-dicarboxylic Acid；8,8,9,9,10,10-hexafluoro-1,2-dimethyl-3,15-dithiatetracyclo[10.3.0.02,6.07,11]pentadeca-4,6,11,13-tetraene-4,14-dicarboxylic acid
• 化学式: C₁₇H₁₀F₆O₄S₂
• 分子量: 456.386
• InChiKey: SBAKKQKNINUASA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene 以 乙腈 为溶剂， 生成 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  具有分子间O-H ... N氢键网络的双晶体中双芳硫醚的光致变色反应。

  摘要：

  具有羧基，1,2-双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（1a）和1a与4的共晶体的二芳基乙烯衍生物的单晶的晶体结构和光致变色性能检查了4'-，2,4'-和2,2'-联吡啶。在晶体1a中，观察到离散的环状结构，其中四个1a分子通过羧基之间的氢键连接。在均晶中，1a的光反应性和光惰性的构象体以1：1的比例存在。在1 a与联吡啶的共晶体中，在1 a和吡啶基之间形成O-HN型氢键，并且所有1 a分子都固定在光反应构象中。均晶1a和共晶均表现出光致变色性能，并且观察到从蓝紫色到青色的颜色变化，

  DOI：

  10.1002/chem.200501148
• 作为产物：
  描述：

  1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene 以 乙腈 为溶剂， 生成 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene
  参考文献：
  名称：

  具有分子间O-H ... N氢键网络的双晶体中双芳硫醚的光致变色反应。

  摘要：

  具有羧基，1,2-双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（1a）和1a与4的共晶体的二芳基乙烯衍生物的单晶的晶体结构和光致变色性能检查了4'-，2,4'-和2,2'-联吡啶。在晶体1a中，观察到离散的环状结构，其中四个1a分子通过羧基之间的氢键连接。在均晶中，1a的光反应性和光惰性的构象体以1：1的比例存在。在1 a与联吡啶的共晶体中，在1 a和吡啶基之间形成O-HN型氢键，并且所有1 a分子都固定在光反应构象中。均晶1a和共晶均表现出光致变色性能，并且观察到从蓝紫色到青色的颜色变化，

  DOI：

  10.1002/chem.200501148

文献信息

• Photochromic Reactions of Diarylethenes in Single Crystals with Intermolecular OH⋅⋅⋅N Hydrogen-Bonding Networks
  作者：Masakazu Morimoto、Masahiro Irie

  DOI：10.1002/chem.200501148

  日期：2006.5.24

  photochromic performance of a single crystal of a diarylethene derivative possessing carboxyl groups, 1,2-bis(5-carboxyl-2-methyl-3-thienyl)perfluorocyclopentene (1 a), and cocrystals of 1 a with 4,4'-, 2,4'-, and 2,2'-bipyridines were examined. In crystal 1 a, a discrete cyclic structure was observed, in which four 1 a molecules are linked through hydrogen bonds between the carboxyl groups. In the homocrystal

  具有羧基，1,2-双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（1a）和1a与4的共晶体的二芳基乙烯衍生物的单晶的晶体结构和光致变色性能检查了4'-，2,4'-和2,2'-联吡啶。在晶体1a中，观察到离散的环状结构，其中四个1a分子通过羧基之间的氢键连接。在均晶中，1a的光反应性和光惰性的构象体以1：1的比例存在。在1 a与联吡啶的共晶体中，在1 a和吡啶基之间形成O-HN型氢键，并且所有1 a分子都固定在光反应构象中。均晶1a和共晶均表现出光致变色性能，并且观察到从蓝紫色到青色的颜色变化，
• Photocyclization of photoswitches with high enantioselectivity in human serum albumin in an artificial environment
  作者：Koichi Kawamura、Ken Osawa、Yuta Watanobe、Yuri Saeki、Naoki Maruyama、Yasushi Yokoyama

  DOI：10.1039/c6cc10197f

  日期：——

  Three photochromic bisthienylethenes exhibited 56 - >99% enantiomer excess in photochemical ring closure upon UV irradiation when incorporated in human serum albumin dissolved in 15% acetonitrile-phosphate buffer solution and incubated...

  当掺入溶于15％乙腈-磷酸盐缓冲液的人血清白蛋白中并孵育后，三种光致变色联苯乙烯在紫外线辐射下的光化学闭环中对映体过量显示56-> 99％。
• Coordination Assemblies of [Mn₄] Single-Molecule Magnets Linked by Photochromic Ligands: Photochemical Control of the Magnetic Properties
  作者：Masakazu Morimoto、Hitoshi Miyasaka、Masahiro Yamashita、Masahiro Irie

  DOI：10.1021/ja903366d

  日期：2009.7.22

  assemblies of a mixed valence tetranuclear [Mn(II)(2)Mn(III)(2)] complex linked by open- and closed-ring isomers of a photochromic diarylethene ligand were synthesized: [Mn(4)(hmp)(6)(dae-o)(2)(ClO(4))(2)] x 6 H(2)O (open-ring form; 1o) and [Mn(4)(hmp)(6)(dae-c)(2)(H(2)O)(2)](ClO(4))(2) x CH(3)CN x 4 H(2)O (closed-ring form; 1c), where Hhmp is 2-hydroxymethylpyridine, and H(2)dae-o and H(2)dae-c are open-

  为了实现单分子磁体 (SMM) 磁性的可逆光开关，混合价四核 [Mn(II)(2)Mn(III)(2)] 配合物的配位组件由开环和闭环异构体连接合成了一种光致变色二芳基乙烯配体：[Mn(4)(hmp)(6)(dae-o)(2)(ClO(4))(2)] x 6 H(2)O（开环形式； 1o) 和 [Mn(4)(hmp)(6)(dae-c)(2)(H(2)O)(2)](ClO(4))(2) x CH(3)CN x 4 H(2)O（闭环形式；1c），其中 Hhmp 是 2-羟甲基吡啶，H(2)dae-o 和 H(2)dae-c 是 1,2- 的开环和闭环异构体分别为双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（H(2)dae）。根据 X 射线晶体学分析，1o 和 1c 具有一维 (1-D) 链结构，重复单元为 [-Mn(4)}-(dae)-]，其中 [Mn(4)] 单元由二芳基乙烯配体通过羧酸根与
• Photochromic 1,2-bis(2′-methyl-5′-(carboxylic acid)-3′-thienyl) perfluorocyclopentene and its Co(II) coordination polymer
  作者：Jing Han、Hao Chen、Zhong Yu、Ping Guo

  DOI：10.1016/j.ica.2017.03.005

  日期：2017.6

  Crystallization from methanol of 1,2-bis(2'-methyl-5'-(carboxylic acid)-3'-thienyl) perfluorocyclopentene (BM-5-CATP, H2L) afforded a new single crystal (H2LMeOH) characterized by single crystal X-ray diffraction analysis, whose structure is different from those of the known crystals crystallized from ethanol, acetone/ hexane or acetonitrile. There are two independent molecules with different conformations in one asymmetric unit of H2L. One is a photo-active anti-parallel conformation in which the reactive C atoms are separated by 3.90 angstrom whereas the other is a photo-inactive parallel conformation in which the reactive C-C distance is 4.42 angstrom. The packing characteristics of the two structures derived from methanol and ethanol were compared and analyzed in detail helped by the corresponding computational analyses. The photo-isomerizations of H2LMeOH in tetrahydrofuran and in solid state occur reversibly upon alternate irradiation with ultraviolet (lambda = 254 nm) and visible light (lambda > 550 nm).Reaction of CoCl2 .6H(2)O with BM-5-CATP in methanol afforded a new complex [CoL(MeOH)(4)](MeOH) (1). Complex 1 is revealed by X-ray crystal diffraction as a 1D zigzag chain, where BM-5-CATP serves as bis-monodentate ligand bridging Co(II) centers in syn-anti fashion. The two thienyl rings in 1 adopt anti-parallel fashions and the distances of 3.80 angstrom between two reactive carbons is short enough for the occurrence of photocyclizations. As expect, complex 1 displayed effective photo-isomerization in crystalline phase with color interconversion between pink and purple, indicating weak suppression of photo-chromism from metal coordination and extensive H bonds as well as Van de Waals contacts. The lambda(max) of 1 (580 nm) in closed form shifted to longer wavelength compared with that of free ligand (576 nm). (C) 2017 Elsevier B.V. All rights reserved.
• Synthesis, Structures, and Magnetic Properties of Two Coordination Assemblies of Mn(III) Single Molecule Magnets Bridged via Photochromic Diarylethene Ligands
  作者：Ahmed Fetoh、Goulven Cosquer、Masakazu Morimoto、Masahiro Irie、Ola El-Gammal、Gaber M. Abu El-Reash、Brian K. Breedlove、Masahiro Yamashita

  DOI：10.1021/acs.inorgchem.8b02578

  日期：2019.2.18

  1′E)-((2,3-dimethylbutane-2,3-diyl)bis(azaneylylidene)) bis(methaneylylidene))diphenol. From X-ray diffraction analyses, the complexes had the following formula: [Mn2(saltmen)2(dae-open)] (1open) and [Mn(saltmen)(dae-close)]·H2O·Et3N (1close). Both complexes crystallized in the C2/c monoclinic space group. In 1open, dae-o2– behaves as a bidentate ligand attached to the outer Mn-saltmen monomer via the

  通过将打开和关闭形式的1,2-双（5-羧基-2-甲基-3-噻吩基）全氟环戊烯（H 2 dae）与[Mn 2（盐）2（H 2 O） ）2 ]（PF 6）2，其中H 2 saltmen = 2,2' - （（1- Ë，1' ë） - （（2,3-二甲基丁烷-2,3-二基）双（azaneylylidene））双（甲叉基））二酚。通过X射线衍射分析，该配合物具有下式：[Mn 2（盐基）2（dae-open）]（1个开放）和[Mn（盐基）（dae-close）]·H 2 O·Et 3N（1关闭）。两种配合物均在C 2 / c单斜晶空间群中结晶。在1开放，DAE-O 2-表现为二齿配体经由羧酸根基团的氧原子连接到外的Mn-saltmen单体，而在1点附近时，DAE-C 2-配体表现为单齿配体附着到外部Mn-盐二聚体仅被光致变色配体的一个羧基取代。该配合物对UV / vis光表现出可逆的光致变色反应，并