9,10-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)anthracene

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,10-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)anthracene
• 英文别名: 2-Hexyl-5-[5-[10-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]anthracen-9-yl]thiophen-2-yl]thiophene；2-hexyl-5-[5-[10-[5-(5-hexylthiophen-2-yl)thiophen-2-yl]anthracen-9-yl]thiophen-2-yl]thiophene
• 化学式: C₄₂H₄₂S₄
• 分子量: 675.059
• InChiKey: ZRSMWXBOSHFSIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.5
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9,10-二溴蒽 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 palladium diacetate 、 potassium carbonate 、 溶剂黄146 、 三甲基丙酮酸 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.08h， 生成 9,10-bis(5'-hexyl-[2,2'-bithiophen]-5-yl)anthracene
  参考文献：
  名称：

  Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials

  摘要：

  We report a new class of multifunctional 9,10-dithienylanthracene-based materials having an anthracene pi-core functionalized at the 9,10 positions with thienyl side-arms of different size and type of substitution. MW-assisted double direct arylation reaction is employed for the first time to synthesize the target molecules in one-step, organometallic free conditions, in only 5 min and yields up to 80% rather than by a multi-step Stile coupling taken as conventional reference approach. DFT calculations reveal a molecular conformation characterized by the thienyl rings orthogonal to the anthracene core. Nevertheless, despite the non-coplanar structure, all compounds exhibited highly crystalline cast films emitting blue light, with an extraordinary variability in morphology and hole mobility up to 8x10(-3) cm(2) V-1 s(-1). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.03.010

文献信息

• Synthesis by MW-assisted direct arylation, side-arms driven self-assembly and functional properties of 9,10-dithienylanthracene orthogonal materials
  作者：Margherita Durso、Massimo Zambianchi、Alberto Zanelli、M. Grazia LoBello、Filippo De Angelis、Stefano Toffanin、Susanna Cavallini、Denis Gentili、Francesca Tinti、Massimiliano Cavallini、Nadia Camaioni、Manuela Melucci

  DOI：10.1016/j.tet.2014.03.010

  日期：2014.9

  We report a new class of multifunctional 9,10-dithienylanthracene-based materials having an anthracene pi-core functionalized at the 9,10 positions with thienyl side-arms of different size and type of substitution. MW-assisted double direct arylation reaction is employed for the first time to synthesize the target molecules in one-step, organometallic free conditions, in only 5 min and yields up to 80% rather than by a multi-step Stile coupling taken as conventional reference approach. DFT calculations reveal a molecular conformation characterized by the thienyl rings orthogonal to the anthracene core. Nevertheless, despite the non-coplanar structure, all compounds exhibited highly crystalline cast films emitting blue light, with an extraordinary variability in morphology and hole mobility up to 8x10(-3) cm(2) V-1 s(-1). (C) 2014 Elsevier Ltd. All rights reserved.