2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane | 773093-00-8

• 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-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane
• 英文别名: 2-(5'-bromo-[2,2'-bithiophen]-5-yl)-1,3-dioxolane；2-[5-(5-Bromothiophen-2-yl)thiophen-2-yl]-1,3-dioxolane；2-[5-(5-bromothiophen-2-yl)thiophen-2-yl]-1,3-dioxolane
• CAS: 773093-00-8
• 化学式: C₁₁H₉BrO₂S₂
• 分子量: 317.227
• InChiKey: JYSGNQMMEATDTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane 在 正丁基锂 、 硼酸三丁酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以61%的产率得到5'-甲酰基-2,2'-联噻吩-5-硼酸(含不同量的酸酐)
  参考文献：
  名称：

  Cyclic Thiourea/Urea Functionalized Triphenylamine-Based Dyes for High-Performance Dye-Sensitized Solar Cells

  摘要：

  Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J(sc)) and open-circuit voltage (V-oc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).

  DOI：

  10.1021/ol4001685
• 作为产物：
  描述：

  2,2'-联二噻吩 在 四氯化碳 、 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.0h， 生成 2-(5’-bromo-[2,2’-bithiophen]-5-yl)-1,3-dioxolane
  参考文献：
  名称：

  Cyclic Thiourea/Urea Functionalized Triphenylamine-Based Dyes for High-Performance Dye-Sensitized Solar Cells

  摘要：

  Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J(sc)) and open-circuit voltage (V-oc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).

  DOI：

  10.1021/ol4001685

文献信息

• Silaindacenodithiophene based organic semiconductor for high performance organic field-effect transistors
  作者：Bogyu Lim、Huabin Sun、Yong-Young Noh

  DOI：10.1016/j.dyepig.2017.07.054

  日期：2017.11

  n-octyl to rhodanine for LGC-D117, and n-octyl to SilDT and ethyl to rhodanine in LGC-D050, to check the effect of alkyl chain length. Top-gate/bottom-contact organic field-effect transistors (OFETs) with LGC-D050 show the best p-type field-effect mobility with a maximum of 1.14 cm2V−1s−1 (average 0.83 ± 0.22 cm2V−1s−1) after 140 °C annealing comparing to LGC-D075 (maximum of 0.90 cm2V−1s−1) and LGC-D117

  为了研究基于硅茚二烯二噻吩（SiIDT）的半导体小分子的结构-性质关系，合成了新的供体-受体型有机小分子LGC-D050，LGC-D075和LGC-D117。这些分子由SilDT作为供电子核和二酮吡咯并吡咯（DPP，LGC-D050和LGC-D117）或一氟-苯并噻二唑（FBT，LGC-D075）作为受电子连接体和烷基金丹宁作为电子接受端组。LGC-D050和LGC-D117均具有相同的主链结构，但侧链不同，例如LGC-D117的2-乙基己基与SilDT相连，罗丹宁的正辛基与n-辛基相连，nLGC-D050中的-辛基对SilDT和乙基对若丹宁，以检查烷基链长的影响。带有LGC-D050的顶栅/底接触有机场效应晶体管（OFET）表现出最佳的p型场效应迁移率，最大值为1.14 cm 2 V -1 s -1（平均0.83±0.22 cm 2 V -1小号-1）后140℃下退火进行比较的0.90厘米LGC-D075（最大2
• 축합고리 유도체 및 이를 포함하는 유기 태양 전지
  申请人：LG CHEM, LTD. 주식회사 엘지화학(120010134563) Corp. No ▼ 110111-2207995BRN ▼107-81-98139

  公开号：KR20150142609A

  公开（公告）日：2015-12-22

  본 명세서는 축합고리 유도체 및 이를 포함하는 유기 태양 전지에 관한 것이다.

  这份规格说明书涉及到集总环导体以及包含它的有机太阳能电池。
• Indolo[2,3-<i>b</i>]carbazole Synthesized from a Double-Intramolecular Buchwald–Hartwig Reaction: Its Application for a Dianchor DSSC Organic Dye
  作者：Jia-Yi Su、Chun-Yuan Lo、Chih-Hung Tsai、Chih-Han Chen、Shu-Hua Chou、Shih-Hung Liu、Pi-Tai Chou、Ken-Tsung Wong

  DOI：10.1021/ol500663b

  日期：2014.6.20

  A new synthetic strategy for indolo[2,3-b]carbazole via a double-intramolecular Buchwald-Hartwig reaction has been established. The N-alkylated indolo[2,3-b]carbazole then was adopted as the geometry-fixed core for the synthesis of a new molecule (ICZDTA) bearing two bithiophene π-bridged 2-cyanoacrylic acid groups as the bidentate anchor. The bidentate anchoring together with efficient HOMO (indolo[2,3-b]carbazole) → LUMO (TiO2 nanocluster) electron transfer leads to the successful development of ICZDTA-based DSSC with a power conversion efficiency of 6.02%.
• Cyclic Thiourea/Urea Functionalized Triphenylamine-Based Dyes for High-Performance Dye-Sensitized Solar Cells
  作者：Zhisheng Wu、Zhongwei An、Xinbing Chen、Pei Chen

  DOI：10.1021/ol4001685

  日期：2013.4.5

  Six cyclic thiourea/urea functionalized triphenylamine-based dyes (AZ1-AZ6) containing 2-cyanoacrylic acid as an acceptor and various linkers (phenyl, biphenyl, and bithiophene) were synthesized. They exhibited high photovoltaic performance owing to an improved short-circuit photocurrent density (J(sc)) and open-circuit voltage (V-oc). Among them, AZ6 bearing a cyclic thiourea group and bithiophene linker showed the highest power conversion efficiency (PCE) up to 7.29%, which was comparable to that of N719 (PCE = 7.36%).