5,5'-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(thiophene-2-carbaldehyde) | 1271313-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 5,5'-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(thiophene-2-carbaldehyde)
• CAS: 1271313-74-6
• 化学式: C₁₆H₈N₂O₂S₂Se
• 分子量: 403.344
• InChiKey: QQNHYQJZDVYCKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  650.8±65.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.92
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,5'-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(thiophene-2-carbaldehyde) 、 对硝基苯乙腈 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以57%的产率得到3,3'-(benzo[c][1,2,5]selenadiazole-4,7-diylbis(thiophene-5,2-diyl))bis(2-(4-nitrophenyl)acrylonitrile)
  参考文献：
  名称：

  Synthesis of benzoselenadiazole-based small molecule and phenylenevinylene copolymer and their application for efficient bulk heterojunction solar cells

  摘要：

  A new low-band gap small molecule (Se-SM), which contains dithyenyl-benzoselenadiazole as central unit and terminal cyanovinylene 4-nitrophenyls, was synthesized. In addition, a new phenylenevinylene copolymer (P) containing dithyenyl-dinitrobenzothiadiazole moieties was synthesized by Heck coupling. Se-SM showed broad absorption band with long-wavelength absorption maximum (lambda(a,max)) at similar to 640 nm and optical band gap (E-g(opt)) of 1.67 eV. Copolymer P had lambda(a,max) around 420 nm and E-g(opt) of 2.31 eV. The dark current-voltage characteristics and incident photon to current efficiency spectra of the devices based on copolymer P and Se-SM indicates that both materials behave as p-type organic semiconductors. The power conversion efficiency (PCE) of the photovoltaic devices based on these materials is low. However, the PCE of the devices fabricated with the blends of copolymer P or Se-SM with PCBM, was improved significantly. The increase is attributed to the formation of bulk heterojunction with increased interfacial area. The effect of the incorporation of Se-SM molecule on the photovoltaic properties of copolymer P: PCBM blend has been also investigated. The overall PCE of the copolymer P: PCBM: Se-SM device is approximately 2.24%, which is further enhanced up to 3.16%, when the thermally annealed blend is used. Therefore, we conclude that the Se-SM molecule increases the light harvesting property of the blend and also provides efficient path for holes and electron in copolymer and PCBM phases, respectively. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2009.11.010
• 作为产物：
  描述：

  4,7-di(thiophen-2-yl)benzo[c][1,2,5]-selenadiazole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以61%的产率得到5,5'-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(thiophene-2-carbaldehyde)
  参考文献：
  名称：

  Synthesis of benzoselenadiazole-based small molecule and phenylenevinylene copolymer and their application for efficient bulk heterojunction solar cells

  摘要：

  A new low-band gap small molecule (Se-SM), which contains dithyenyl-benzoselenadiazole as central unit and terminal cyanovinylene 4-nitrophenyls, was synthesized. In addition, a new phenylenevinylene copolymer (P) containing dithyenyl-dinitrobenzothiadiazole moieties was synthesized by Heck coupling. Se-SM showed broad absorption band with long-wavelength absorption maximum (lambda(a,max)) at similar to 640 nm and optical band gap (E-g(opt)) of 1.67 eV. Copolymer P had lambda(a,max) around 420 nm and E-g(opt) of 2.31 eV. The dark current-voltage characteristics and incident photon to current efficiency spectra of the devices based on copolymer P and Se-SM indicates that both materials behave as p-type organic semiconductors. The power conversion efficiency (PCE) of the photovoltaic devices based on these materials is low. However, the PCE of the devices fabricated with the blends of copolymer P or Se-SM with PCBM, was improved significantly. The increase is attributed to the formation of bulk heterojunction with increased interfacial area. The effect of the incorporation of Se-SM molecule on the photovoltaic properties of copolymer P: PCBM blend has been also investigated. The overall PCE of the copolymer P: PCBM: Se-SM device is approximately 2.24%, which is further enhanced up to 3.16%, when the thermally annealed blend is used. Therefore, we conclude that the Se-SM molecule increases the light harvesting property of the blend and also provides efficient path for holes and electron in copolymer and PCBM phases, respectively. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.orgel.2009.11.010