5-[15-(5-Formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-24-(5-iodothiophen-2-yl)-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde | 898257-20-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 5-[15-(5-Formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-24-(5-iodothiophen-2-yl)-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde
• CAS: 898257-20-0
• 化学式: C₇₇H₉₅IO₂S₃
• 分子量: 1275.7
• InChiKey: GPNCWTZOEBJSBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  30
• 重原子数：
  83
• 可旋转键数：
  35
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[15-(5-Formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-24-(5-iodothiophen-2-yl)-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde 、 乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以45%的产率得到5-[24-[5-[2-[5-[15,24-Bis(5-formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophen-2-yl]ethynyl]thiophen-2-yl]-15-(5-formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Nanosized Rigid π-Conjugated Molecular Heterojunctions with Multi[60]fullerenes:  Facile Synthesis and Photophysical Properties

  摘要：

  A series of large, rigid, new, well-defined, D-pi-B-A compounds with three chromophores(truxene moieties at the core, conjugated oligothiophenes as the branch bridges, and [60]pyrrolidinofullerene (C-60) segments as the end-capped groups) have been facilely developed in this contribution. Oligothiophene-functionalized truxene derivatives 1-29 are prepared by the Suzuki, the Sonogashira, and the Negishi cross-coupling reactions catalyzed by Pd(PPh3)(4) as well as the McMurry reaction, respectively. The 1,3-dipolar cycloaddition of the oligomers with C-60 and N-methylglycine yields a new family of star-shaped D-pi-B-A derivatives end-capped with pyrrolidinofullerene moieties as the active materials for photovoltaic devices in which one, two, three, or four C-60 moieties are allocated at the peripheral position of well-defined compounds, respectively. We also investigate the UV-vis and photoluminescence behaviors of these pyrrolidinofullerene-functionalized derivatives. The emission is obviously quenched after the inducement of the C-60 moieties. We also observe that the emission intensity is decreased with the increase in the number of C-60 moieties.

  DOI：

  10.1021/jo060097t
• 作为产物：
  描述：

  5-[24-(5-Formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-15-thiophen-2-yl-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 2.0h， 以90%的产率得到5-[15-(5-Formylthiophen-2-yl)-9,9,18,18,27,27-hexahexyl-24-(5-iodothiophen-2-yl)-6-heptacyclo[18.7.0.02,10.03,8.011,19.012,17.021,26]heptacosa-1(20),2(10),3(8),4,6,11(19),12(17),13,15,21(26),22,24-dodecaenyl]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Nanosized Rigid π-Conjugated Molecular Heterojunctions with Multi[60]fullerenes:  Facile Synthesis and Photophysical Properties

  摘要：

  A series of large, rigid, new, well-defined, D-pi-B-A compounds with three chromophores(truxene moieties at the core, conjugated oligothiophenes as the branch bridges, and [60]pyrrolidinofullerene (C-60) segments as the end-capped groups) have been facilely developed in this contribution. Oligothiophene-functionalized truxene derivatives 1-29 are prepared by the Suzuki, the Sonogashira, and the Negishi cross-coupling reactions catalyzed by Pd(PPh3)(4) as well as the McMurry reaction, respectively. The 1,3-dipolar cycloaddition of the oligomers with C-60 and N-methylglycine yields a new family of star-shaped D-pi-B-A derivatives end-capped with pyrrolidinofullerene moieties as the active materials for photovoltaic devices in which one, two, three, or four C-60 moieties are allocated at the peripheral position of well-defined compounds, respectively. We also investigate the UV-vis and photoluminescence behaviors of these pyrrolidinofullerene-functionalized derivatives. The emission is obviously quenched after the inducement of the C-60 moieties. We also observe that the emission intensity is decreased with the increase in the number of C-60 moieties.

  DOI：

  10.1021/jo060097t