3,3',3",3''',3'''',3''''',3'''''',3'''''''-octahexyl-2,2':5',5":2",2''':5''',5'''':2'''',2''''':5''''',5'''''':2'''''',2'''''''-octithiophene | 170702-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,3',3",3''',3'''',3''''',3'''''',3'''''''-octahexyl-2,2':5',5":2",2''':5''',5'''':2'''',2''''':5''''',5'''''':2'''''',2'''''''-octithiophene
• 英文别名: 3,3',3''',3'''',3''''''',4'',4'''',4''''''-octahexyl-octithiophene；3-Hexyl-2-[3-hexyl-5-[4-hexyl-5-[3-hexyl-5-[4-hexyl-5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-[4-hexyl-5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophene；3-hexyl-2-[3-hexyl-5-[4-hexyl-5-[3-hexyl-5-[4-hexyl-5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-[4-hexyl-5-(3-hexylthiophen-2-yl)thiophen-2-yl]thiophene
• CAS: 170702-14-4
• 化学式: C₈₀H₁₁₄S₈
• 分子量: 1332.31
• InChiKey: FSDRTFYRRWLALG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  35
• 重原子数：
  88
• 可旋转键数：
  47
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  226
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3',3",3''',3'''',3''''',3'''''',3'''''''-octahexyl-2,2':5',5":2",2''':5''',5'''':2'''',2''''':5''''',5'''''':2'''''',2'''''''-octithiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 0.5h， 以91%的产率得到5,5'''''''-dibromo-3,3',3",3''',3'''',3''''',3'''''',3'''''''-octahexyl-2,2':5',5":2",2''':5''',5'''':2'''',2''''':5''''',5'''''':2'''''',2'''''''-octithiophene
  参考文献：
  名称：

  Synthesis and Properties ofα,ω-Disubstituted Oligo(3-hexylthiophene)s and Oligothienoquinonoids in Head-to-head Orientation

  摘要：

  合成了两种头对头取向的高度有序的寡聚（3-己基噻吩），一系列α,ω-二取代的寡噻吩和一系列双（氰亚甲基）寡噻吩醌类化合物。基于电子光谱和循环伏安法，讨论了这些化合物的性质。

  DOI：

  10.1246/bcsj.68.2363
• 作为产物：
  描述：

  5-溴-3,3'-二己基-2,2'-联噻吩 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 iron(III)-acetylacetonate 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 1.83h， 生成 3,3',3",3''',3'''',3''''',3'''''',3'''''''-octahexyl-2,2':5',5":2",2''':5''',5'''':2'''',2''''':5''''',5'''''':2'''''',2'''''''-octithiophene
  参考文献：
  名称：

  Synthesis and Properties ofα,ω-Disubstituted Oligo(3-hexylthiophene)s and Oligothienoquinonoids in Head-to-head Orientation

  摘要：

  合成了两种头对头取向的高度有序的寡聚（3-己基噻吩），一系列α,ω-二取代的寡噻吩和一系列双（氰亚甲基）寡噻吩醌类化合物。基于电子光谱和循环伏安法，讨论了这些化合物的性质。

  DOI：

  10.1246/bcsj.68.2363

文献信息

• A Successful Chemical Strategy To Induce Oligothiophene Self-Assembly into Fibers with Tunable Shape and Function
  作者：Francesca Di Maria、Pasquale Olivelli、Massimo Gazzano、Alberto Zanelli、Mariano Biasiucci、Giuseppe Gigli、Denis Gentili、Pasquale D’Angelo、Massimiliano Cavallini、Giovanna Barbarella

  DOI：10.1021/ja2014949

  日期：2011.6.8

  Functional supramolecular architectures for bottom-up organic nano- and microtechnology are a high priority research topic. We discovered a new recognition algorithm, resulting from the combination of thioalkyl substituents and head-to-head regiochemistry of substitution, to induce the spontaneous self-assembly of sulfur overrich octathiophenes into supramolecular crystalline fibers combining high charge mobility and intense fluorescence. The fibers were grown on various types of surfaces either as superhelices or straight rods depending on molecular structure. Helical fibers directly grown on a field effect transistor displayed efficient charge mobility and intrinsic 'memory effect'. Despite the fact that the oligomers did not have chirality centers, one type of hand-helicity was always predominant in helical fibers, due to the interplay of molecular atropisomerism and sup ramolecular helicity induced by terminal substituents. Finally, we found that the new sulfur overrich oligothiophenes can easily be prepared in high yields through ultrasound and microwave assistance in green conditions.
• Synthesis and Properties of<i>α</i>,<i>ω</i>-Disubstituted Oligo(3-hexylthiophene)s and Oligothienoquinonoids in Head-to-head Orientation
  作者：Hiroyuki Higuchi、Taketoshi Nakayama、Haruki Koyama、Juro Ojima、Tatsuo Wada、Hiroyuki Sasabe

  DOI：10.1246/bcsj.68.2363

  日期：1995.8

  The two types of highly-ordered oligo(3-hexylthiophene)s in head-to-head orientation, a series of α,ω-disubstituted oligothiophenes and a series of bis(dicyanomethylene)oligothienoquinonoids, were synthesized. The properties of these compounds are discussed on the basis of the electronic spectra and cyclic voltammetry.

  合成了两种头对头取向的高度有序的寡聚（3-己基噻吩），一系列α,ω-二取代的寡噻吩和一系列双（氰亚甲基）寡噻吩醌类化合物。基于电子光谱和循环伏安法，讨论了这些化合物的性质。
• Synthesis and Photovoltaic Properties of Regioregular Head-to-Head Substituted Thiophene Hexadecamers
  作者：Francesca Di Maria、Massimo Gazzano、Alberto Zanelli、Giuseppe Gigli、Anna Loiudice、Aurora Rizzo、Mariano Biasiucci、Elisabetta Salatelli、Pasquale D’ Angelo、Giovanna Barbarella

  DOI：10.1021/ma301678g

  日期：2012.10.23

  We describe the expedient synthesis of regioregular thiophene hexadecamers head-to-head (hh) substituted with hexyl and hexylthio grous. The synthesis was carried out by means of a sequence of ultrasound-assisted selective monobrominations and microwave-assisted Suzuki reactions using 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in THF:water. The hexadecamers, which are very soluble in organic solvents, were investigated in solution and thin film by a variety of techniques (UV, PL, CV, X-ray diffraction, FET charge mobility, SKFM) with the aim of elucidating the effect of the sulfur spacer on morphology and functional properties. We show that the sulfur spacer compensates for the decrease in pi-pi conjugation caused by the hh regiochemistry and that the lambda(max) value and redox potentials of the S-alkyl-substituted hexadecamer are similar to those of head-to-tail substituted poly(3-hexylthiophene). Measurements in field effect transistor devices showed that the alkylthio-substituted hexadecamer is a p-type semiconductor while the alkyl-substituted counterpart in the same conditions is not electroactive. Scanning Kelvin force microscopy measurements showed that a blend of the alkylthio-substituted hexadecamer with PCBM displays photovoltaic behavior under illumination. In agreement with this, a bulk heterojunction cell fabricated employing the same blend displayed near 1.5% conversion efficiency without addition of additives or device optimization.