5,12-bis(4-methylphenyl)-6,11-diphenylnaphthacene | 127257-72-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 5,12-bis(4-methylphenyl)-6,11-diphenylnaphthacene
• 英文别名: 5,12-Bis(4-methylphenyl)-6,11-diphenyltetracene
• CAS: 127257-72-1
• 化学式: C₄₄H₃₂
• 分子量: 560.738
• InChiKey: KBCCRCPEIKSBMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  6,11-di-p-tolyl-naphthacene-5,12-dione 在 正丁基锂 、 氢碘酸 作用下， 以 乙醚 为溶剂， 生成 5,12-bis(4-methylphenyl)-6,11-diphenylnaphthacene
  参考文献：
  名称：

  Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties

  摘要：

  Correlations among the molecular structure, crystal structure, electronic structure, and charge-carrier transport phenomena have been derived from six congeners (2-7) of rubrene (1). The congeners were synthesized via a three-step route from known 6,11-dichloro-5,12-tetracenedione. After crystallization, their packing structures were solved using single-crystal X-ray diffraction. Rubrenes 5-7 maintain the orthorhombic features of the parent rubrene (1) in their solid-state packing structures. Control of the packing structure in 5-7 provided the first series of systematically manipulated rubrenes that preserve the pi-stacking motif of 1. Density functional theory calculations were performed at the B3LYP/6-31G(d,p) level of theory to evaluate the geometric and electronic structure of each derivative and reveal that key properties of rubrene (1) have been maintained. Intermolecular electronic couplings (transfer integrals) were calculated for each derivative to determine the propensity for charge-carrier transport. For rubrenes 5-7, evaluations of the transfer integrals and periodic electronic structures suggest these derivatives should exhibit transport characteristics equivalent to, or in some cases improved on, those of the parent rubrene (1), as well as the potential for ambipolar behavior. Single crystal field-effect transistors were fabricated for 5-7, and these derivatives show ambipolar transport as predicted. Although device architecture has yet to be fully optimized, maximum hole (electron) mobilities of 1.54 (0.28) cm(2) V-1 s(-1) were measured for rubrene 5. This work lays a foundation to improve our understanding of charge carrier transport phenomena in organic single crystal semiconductors through the correlation of designed molecular and crystallographic changes to electronic and transport properties.

  DOI：

  10.1021/cm400736s

文献信息

• Regioselective synthesis of substituted rubrenes
  作者：Jeffrey A. Dodge、J. D. Bain、A. Richard Chamberlin

  DOI：10.1021/jo00300a043

  日期：1990.6
• DODGE, JEFFREY A.;BAIN, J. D.;CHAMBERLIN, A. RICHARD, J. ORG. CHEM., 55,(1990) N3, C. 4190-4198
  作者：DODGE, JEFFREY A.、BAIN, J. D.、CHAMBERLIN, A. RICHARD

  DOI：——

  日期：——
• Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties
  作者：Kathryn A. McGarry、Wei Xie、Christopher Sutton、Chad Risko、Yanfei Wu、Victor G. Young、Jean-Luc Brédas、C. Daniel Frisbie、Christopher J. Douglas

  DOI：10.1021/cm400736s

  日期：2013.6.11

  Correlations among the molecular structure, crystal structure, electronic structure, and charge-carrier transport phenomena have been derived from six congeners (2-7) of rubrene (1). The congeners were synthesized via a three-step route from known 6,11-dichloro-5,12-tetracenedione. After crystallization, their packing structures were solved using single-crystal X-ray diffraction. Rubrenes 5-7 maintain the orthorhombic features of the parent rubrene (1) in their solid-state packing structures. Control of the packing structure in 5-7 provided the first series of systematically manipulated rubrenes that preserve the pi-stacking motif of 1. Density functional theory calculations were performed at the B3LYP/6-31G(d,p) level of theory to evaluate the geometric and electronic structure of each derivative and reveal that key properties of rubrene (1) have been maintained. Intermolecular electronic couplings (transfer integrals) were calculated for each derivative to determine the propensity for charge-carrier transport. For rubrenes 5-7, evaluations of the transfer integrals and periodic electronic structures suggest these derivatives should exhibit transport characteristics equivalent to, or in some cases improved on, those of the parent rubrene (1), as well as the potential for ambipolar behavior. Single crystal field-effect transistors were fabricated for 5-7, and these derivatives show ambipolar transport as predicted. Although device architecture has yet to be fully optimized, maximum hole (electron) mobilities of 1.54 (0.28) cm(2) V-1 s(-1) were measured for rubrene 5. This work lays a foundation to improve our understanding of charge carrier transport phenomena in organic single crystal semiconductors through the correlation of designed molecular and crystallographic changes to electronic and transport properties.