2,2'-(5',5''-(2,3-diphenylthieno[3,4-b]pyrazine-5,7-diyl)bis(3',4'-diethyl-2,2'-bithien-5',5-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile | 1357600-04-4

• 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: 2,2'-(5',5''-(2,3-diphenylthieno[3,4-b]pyrazine-5,7-diyl)bis(3',4'-diethyl-2,2'-bithien-5',5-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile
• 英文别名: 2-[[5-[5-[5-[5-[5-(2,2-Dicyanoethenyl)thiophen-2-yl]-3,4-diethylthiophen-2-yl]-2,3-diphenylthieno[3,4-b]pyrazin-7-yl]-3,4-diethylthiophen-2-yl]thiophen-2-yl]methylidene]propanedinitrile；2-[[5-[5-[5-[5-[5-(2,2-dicyanoethenyl)thiophen-2-yl]-3,4-diethylthiophen-2-yl]-2,3-diphenylthieno[3,4-b]pyrazin-7-yl]-3,4-diethylthiophen-2-yl]thiophen-2-yl]methylidene]propanedinitrile
• CAS: 1357600-04-4
• 化学式: C₅₀H₃₆N₆S₅
• 分子量: 881.206
• InChiKey: GOFLIEOYRVCKAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  61
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  235
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2-(2-噻吩基)-1,3-二氧戊环 在 哌啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium phosphate 、 正丁基锂 、 水 、 对甲苯磺酸 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 27.67h， 生成 2,2'-(5',5''-(2,3-diphenylthieno[3,4-b]pyrazine-5,7-diyl)bis(3',4'-diethyl-2,2'-bithien-5',5-diyl))bis(methan-1-yl-1-ylidene)dimalononitrile
  参考文献：
  名称：

  Synthesis and characterizations of red/near-IR absorbing A–D–A–D–A-type oligothiophenes containing thienothiadiazole and thienopyrazine central units

  摘要：

  一系列π共轭的A–D–A–D–A型寡聚噻吩（1–3）被开发为红/近红外吸收剂，核心为杂环噻吡[3,4-c][1,2,5]噻二唑（TTDA）或噻吡[3,4-b]吡嗪（TP），末端受体基团为二氰乙烯（DCV）或三氟乙酰基（TFA）。所得到的寡聚物通过紫外-可见光光谱、循环伏安法和热分析进行了表征。发现这些寡聚物的低能吸收带在溶液中位于620–707 nm，而在薄膜中则位于695–830 nm。理论研究表明，双环非经典噻吩的插入使得共轭主链产生部分醌式特性，从而降低了带隙。通过电化学测量得到的1–3的HOMO–LUMO能量适合与富勒烯-C60作为受体结合，作为平面异质结太阳能电池中的供体材料，该电池由真空沉积制备。这些包含低带隙寡聚物的器件在空气质量（AM）1.5G照射下，展现出高达0.60的填充因子（FF）以及最高1.3%的功率转换效率。外量子效率（EQE）光谱清晰地显示出低能吸收对整个光电流的贡献。

  DOI：

  10.1039/c2jm13285k

文献信息

• Synthesis and characterizations of red/near-IR absorbing A–D–A–D–A-type oligothiophenes containing thienothiadiazole and thienopyrazine central units
  作者：Simon Steinberger、Amaresh Mishra、Egon Reinold、Elena Mena-Osteritz、Heiko Müller、Christian Uhrich、Martin Pfeiffer、Peter Bäuerle

  DOI：10.1039/c2jm13285k

  日期：——

  A series of π-conjugated A–D–A–D–A-type oligothiophenes (1–3) comprising heterocyclic thieno[3,4-c][1,2,5]thiadiazole (TTDA) or thieno[3,4-b]pyrazine (TP) as the core and dicyanovinyl (DCV) or trifluoroacetyl (TFA) as terminal acceptor groups have been developed as red/near-IR absorbers. The resulting oligomers were characterized by UV-Vis spectroscopy, cyclic voltammetry and thermal analysis. The low energy absorption band of these oligomers was located at 620–707 nm in solution and at 695–830 nm in thin films. Theoretical studies reveal that the insertion of the bicyclic nonclassical thiophenes to the conjugated backbone imposed partial quinoidal character to the resulting oligomers and thus reduced the band gap. HOMO–LUMO energies of 1–3 derived from electrochemical measurements were found to be suitable for the use as donor material in combination with fullerene-C60 as acceptor in planar heterojunction solar cells prepared by vacuum deposition. Such devices incorporating these low band gap oligomers exhibited high FF values up to 0.60, and power conversion efficiencies of up to 1.3% under air mass (AM) 1.5G illumination. External quantum efficiency (EQE) spectra clearly showed the contribution of the low energy absorption to the overall photocurrent.

  一系列π共轭的A–D–A–D–A型寡聚噻吩（1–3）被开发为红/近红外吸收剂，核心为杂环噻吡[3,4-c][1,2,5]噻二唑（TTDA）或噻吡[3,4-b]吡嗪（TP），末端受体基团为二氰乙烯（DCV）或三氟乙酰基（TFA）。所得到的寡聚物通过紫外-可见光光谱、循环伏安法和热分析进行了表征。发现这些寡聚物的低能吸收带在溶液中位于620–707 nm，而在薄膜中则位于695–830 nm。理论研究表明，双环非经典噻吩的插入使得共轭主链产生部分醌式特性，从而降低了带隙。通过电化学测量得到的1–3的HOMO–LUMO能量适合与富勒烯-C60作为受体结合，作为平面异质结太阳能电池中的供体材料，该电池由真空沉积制备。这些包含低带隙寡聚物的器件在空气质量（AM）1.5G照射下，展现出高达0.60的填充因子（FF）以及最高1.3%的功率转换效率。外量子效率（EQE）光谱清晰地显示出低能吸收对整个光电流的贡献。