thiophene-2,5-diylbis(mesitylmethanol) | 223921-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: thiophene-2,5-diylbis(mesitylmethanol)
• 英文别名: [5-[Hydroxy-(2,4,6-trimethylphenyl)methyl]thiophen-2-yl]-(2,4,6-trimethylphenyl)methanol；[5-[hydroxy-(2,4,6-trimethylphenyl)methyl]thiophen-2-yl]-(2,4,6-trimethylphenyl)methanol
• CAS: 223921-64-0
• 化学式: C₂₄H₂₈O₂S
• 分子量: 380.551
• InChiKey: KGVHJWDSVSOCFB-UHFFFAOYSA-N

物化性质

• 沸点：
  568.5±45.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  thiophene-2,5-diylbis(mesitylmethanol) 在 三氟化硼乙醚 、 三氯氧磷 作用下， 生成 5,10-dimesityl-1,14-diformyl-16-thiatripyrromethane
  参考文献：
  名称：

  Synthesis of pseudoaromatic expanded porphyrin analogues

  摘要：

  Optically active expanded porphyrins bearing thiophene were synthesized by Schiff base forming reaction. The condensation of thiophene containing 1,14-bisformyl tripyrrane with aromatic diamines Failed to give desired macrocycles but condensation with aliphatic 1,2-diamines gave the desired products. The macrocycles synthesized tend to maintain 18 pi system and the ethylene bridge shows somewhat resistance toward oxidation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00044-1
• 作为产物：
  描述：

  噻吩 、 2,4,6-三甲基苯甲醛 在 正丁基锂 作用下， 以87%的产率得到thiophene-2,5-diylbis(mesitylmethanol)
  参考文献：
  名称：

  Synthesis of pseudoaromatic expanded porphyrin analogues

  摘要：

  Optically active expanded porphyrins bearing thiophene were synthesized by Schiff base forming reaction. The condensation of thiophene containing 1,14-bisformyl tripyrrane with aromatic diamines Failed to give desired macrocycles but condensation with aliphatic 1,2-diamines gave the desired products. The macrocycles synthesized tend to maintain 18 pi system and the ethylene bridge shows somewhat resistance toward oxidation. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00044-1

文献信息

• Carbazole-Based Porphyrins: Synthesis, Structure–Photophysical Property Correlations, and Mercury Ion Sensing
  作者：Arumugam Kalaiselvan、Isukapalli Sai Vamsi Krishna、Anjana Prasad Nambiar、Aathira Edwin、Vennapusa Sivaranjana Reddy、Sabapathi Gokulnath

  DOI：10.1021/acs.orglett.0c01500

  日期：2020.6.5

  The synthesis of a new class of carbazole based macrocycles via [3 + 1] acid-catalyzed condensation is reported. Spectroscopic investigations and computational studies imply that these macrocycles have a large influence on the electronic structure in comparison to previously reported carbazole based macrocycles. Macrocycle 8 bearing a furan ring reversibly binds aqueous Hg2+ with high affinity over

  报道了通过[3 + 1]酸催化的缩合反应合成一类新的咔唑类大环化合物。光谱研究和计算研究表明，与以前报道的基于咔唑的大环化合物相比，这些大环化合物对电子结构的影响很大。带有呋喃环的大环8与其他M n +离子具有高亲和力，可逆地结合Hg 2+水溶液。检测限（LOD）约为。100 nM。通过X射线衍射分析确认了Hg 2+的结合。
• Core-Modified<i>meso</i>-Aryl Hexaphyrins with an Internal Thiophene Bridge: Structure, Aromaticity, and Photodynamics
  作者：Ganesan Karthik、Mahima Sneha、V. Prabhu Raja、Jong Min Lim、Dongho Kim、A. Srinivasan、Tavarekere K. Chandrashekar

  DOI：10.1002/chem.201203737

  日期：2013.2.4

  synthesis of core‐modified meso aryl hexaphyrins with an internal thiophene bridge is reported. Introduction of the thiophene bridge alters the electronic structure as well as the π‐electron circuit, resulting in increases in singlet lifetime (τs) and the two‐photon absorption (TPA) cross‐section. Furthermore, for the sulfur derivative, the internal bridging thiophene participates in a π‐electron conjugation

  捷径出击：报道了带有内部噻吩桥的核心修饰的内消旋芳基六卟啉的合成。噻吩桥改变电子结构以及π电子电路，从而在单寿命（增加的引入τ小号）和双光子吸收（TPA）截面。此外，对于硫衍生物，内部桥联噻吩参与π电子共轭途径。
• One-Pot Synthesis of Core-Modified <i>meso</i>-Aryl Calix[5]phyrin and N-Fused [24]Pentaphyrin
  作者：Sabapathi Gokulnath、Tavarekere K. Chandrashekar

  DOI：10.1021/ol7029728

  日期：2008.2.1

  Synthesis and characterization of core-modified meso-aryl calix[5]phyrins and N-fused pentaphyrins are reported.

  报道了核修饰的中芳基杯[5]卟啉和N稠合的五卟啉的合成和表征。
• Cyclobis[2,5-(thiophenedimethane)-4,4′-(triphenylamine)] versus Its <i>S</i>,<i>S</i>-Dioxidized Macrocycle: Global Antiaromaticity and Intramolecular Dynamics
  作者：Fernando Lopez-Garcia、Shaoqiang Dong、Yi Han、Johnathan Joo Cheng Lee、Pei Wen Ng、Chunyan Chi

  DOI：10.1021/acs.orglett.1c02200

  日期：2021.8.20

  macrocycles containing benzenoid rings rarely show global aromaticity/antiaromaticity. Herein, we report an annulene-like macrocycle CBTT and its S,S-dioxidized macrocycle DOCBTT with alternative quinoidal thiophene/1,1-dioxide thiophene and triphenyl amine moieties. They both showed temperature-dependent intramolecular dynamics and global antiaromatic character with 32π electrons at low temperature. However

  含有苯环的完全共轭大环很少表现出整体芳香性/反芳香性。在此，我们报告一个轮烯状的大环化合物CBTT及其小号，š -dioxidized大环DOCBTT具有替代醌型噻吩/ 1,1-二氧化物噻吩和三苯基胺部分。它们都显示出温度依赖性分子内动力学和低温下具有 32π 电子的全局反芳香特性。然而，CBTT和DOCBTT具有不同的共轭途径。
• Core-modified porphyrins. Part 4: Steric effects on photophysical and biological properties in vitro
  作者：Youngjae You、Scott L. Gibson、Russell Hilf、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1016/j.bmc.2004.12.048

  日期：2005.3

  21,23-Dithiaporphyrins (2-10) were designed and prepared as analogues of 5,20-diphenyl-10,15-bis(4-carboxylatomethoxy)phenyl-21,23-dithiaporphyrin (1) to examine the impact of steric bulk at the 5- and 20-meso positions as well as the impact of symmetry. Changes at the meso positions had minimal impact on the UV-vis-near-IR absorption spectra, quantum yields for the generation of singlet oxygen, and quantum yields for fluorescence and some impact on values of the octanol/water partition coefficient. Of the compounds 1-10, 5-phenyl-20-(2-thienyl)-10,15-bis-(4-carboxylatomethoxy-phenyl)-21,23-dithiaporphyrin (3) showed the greatest phototoxicity toward cultured R3230AC cells, with 68% cell kill at 1 x 10(-7) M and irradiation with 5 J cm(-2) of 350-750 nm light. Results in this study suggest that smaller substituents on the meso ring and less symmetrical compounds are more effective as photosensitizers than compounds with two bulky substituents at adjoining meso sites and a higher symmetry. The mitochondria appear to be involved in the process of phototoxicity as determined by the inhibition of whole cell cytochrome c oxidase activity in cells treated with 3 and light. No impact upon mitochondrial cytochrome c oxidase activity was observed in cells treated with 3 and no light. Fluorescence microscopy studies suggest that the mitochondria are not initial sites of accumulation of 3. (c) 2004 Elsevier Ltd. All rights reserved.