1-(3-溴噻吩-2-基)十二烷基-1-酮 | 950223-94-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-溴噻吩-2-基)十二烷基-1-酮
• 英文名称: 1-(3-Bromothiophen-2-YL)dodecan-1-one
• 英文别名: 1-(3-bromothiophen-2-yl)dodecan-1-one
• CAS: 950223-94-6
• 化学式: C₁₆H₂₅BrOS
• mdl: MFCD22964333
• 分子量: 345.344
• InChiKey: FTRJWVKWSBCKSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.687
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-溴噻吩-2-基)十二烷基-1-酮 在 喹啉 、 水 、 铜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 3-十一烷基噻吩并[3,2-b]噻吩
  参考文献：
  名称：

  氯化端基的异构效应对有效的太阳能转化的影响

  摘要：

  分子结构具有细微差异的异构体通常表现出不同的电子/光电性能，电荷传输行为和光伏性能。在这项工作中，我们描述了BTIC-2Cl-γ，BTIC-2Cl-δ和BTIC-2Cl-β这三个异构体，具有受体-供体-受体-供体-受体（AD-AD-AD-A）结构，其中稠合的苯并噻二唑是供体（D）单元，并且在苯稠合的端基的δ，β或γ位置取代的单个氯原子是受体（A）单元。通常，发现氯原子位置的变化会导致吸收率，能级和光伏性能的显着不同。与BTIC-2Cl-δ相比，BTIC-2Cl-γ异构体显示出相似的UV / Vis吸收，能级和分子堆积，但光伏性能略好。BTIC-2Cl-δ的晶体学分析表明，由于Cl⋯S，Cl⋯π和Cl⋯N的非共价相互作用，分子容易形成三维（3D）网络。当与PBDB-TF作为电子给体材料共混时，基于BTIC- 2Cl-γ的器件表现出高达15.04％的更高功率转换效率（PCE），而电压（V oc）则提高了0

  DOI：

  10.1039/d0ta09306h
• 作为产物：
  描述：

  3-溴噻吩 、 月桂酰氯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(3-溴噻吩-2-基)十二烷基-1-酮
  参考文献：
  名称：

  氯化端基的异构效应对有效的太阳能转化的影响

  摘要：

  分子结构具有细微差异的异构体通常表现出不同的电子/光电性能，电荷传输行为和光伏性能。在这项工作中，我们描述了BTIC-2Cl-γ，BTIC-2Cl-δ和BTIC-2Cl-β这三个异构体，具有受体-供体-受体-供体-受体（AD-AD-AD-A）结构，其中稠合的苯并噻二唑是供体（D）单元，并且在苯稠合的端基的δ，β或γ位置取代的单个氯原子是受体（A）单元。通常，发现氯原子位置的变化会导致吸收率，能级和光伏性能的显着不同。与BTIC-2Cl-δ相比，BTIC-2Cl-γ异构体显示出相似的UV / Vis吸收，能级和分子堆积，但光伏性能略好。BTIC-2Cl-δ的晶体学分析表明，由于Cl⋯S，Cl⋯π和Cl⋯N的非共价相互作用，分子容易形成三维（3D）网络。当与PBDB-TF作为电子给体材料共混时，基于BTIC- 2Cl-γ的器件表现出高达15.04％的更高功率转换效率（PCE），而电压（V oc）则提高了0

  DOI：

  10.1039/d0ta09306h

文献信息

• Isomeric effects of chlorinated end groups on efficient solar conversion
  作者：Daize Mo、Hui Chen、Jiadong Zhou、Liang Han、Yulin Zhu、Pengjie Chao、Nan Zheng、Zengqi Xie、Feng He

  DOI：10.1039/d0ta09306h

  日期：——

  (PCE) of up to 15.04% with an increased voltage (Voc) of 0.90 V, which was better than that of BTIC-2Cl-δ-based devices (14.13%) and much higher than that of BTIC-2Cl-β-based devices (7.39%). Our studies demonstrate that having the chlorine atom at the different positions of the end groups clearly affects the photovoltaic properties of the resulting acceptors.

  分子结构具有细微差异的异构体通常表现出不同的电子/光电性能，电荷传输行为和光伏性能。在这项工作中，我们描述了BTIC-2Cl-γ，BTIC-2Cl-δ和BTIC-2Cl-β这三个异构体，具有受体-供体-受体-供体-受体（AD-AD-AD-A）结构，其中稠合的苯并噻二唑是供体（D）单元，并且在苯稠合的端基的δ，β或γ位置取代的单个氯原子是受体（A）单元。通常，发现氯原子位置的变化会导致吸收率，能级和光伏性能的显着不同。与BTIC-2Cl-δ相比，BTIC-2Cl-γ异构体显示出相似的UV / Vis吸收，能级和分子堆积，但光伏性能略好。BTIC-2Cl-δ的晶体学分析表明，由于Cl⋯S，Cl⋯π和Cl⋯N的非共价相互作用，分子容易形成三维（3D）网络。当与PBDB-TF作为电子给体材料共混时，基于BTIC- 2Cl-γ的器件表现出高达15.04％的更高功率转换效率（PCE），而电压（V oc）则提高了0
• Design, synthesis and photovoltaic properties of a new D–π–A polymer with extended π-bridge units
  作者：Xia Guo、Maojie Zhang、Lijun Huo、Feng Xu、Yue Wu、Jianhui Hou

  DOI：10.1039/c2jm32931j

  日期：——

  New low band gap copolymers PBDTT–DTTBT and PBDTT–DTBT using BDT-T and BT as donor and acceptor, with different π-bridge units thieno[3,2-b]thiophene and thiophene, respectively, were synthesized. The absorption spectra, electronic energy levels, and photovoltaic properties of the polymers were characterized. PBDTT–DTTBT and PBDTT–DTBT films show broad absorption in the visible range with an absorption edge at over 751 nm, and possess relatively low-lying HOMO levels at −5.11 eV and 5.15 eV. A high hole mobility of 1.97 × 10−3 cm2 V−1 s−1 was recorded for PBDTT–DTTBT, that is two orders of magnitude higher than PBDTT–DTBT (1.58 × 10−5 cm2 V−1 s−1), which is ascribed to the application of thieno[3,2-b]thiophene as π-bridge units. The PCE of the PSC device based on PBDTT–DTTBT/PC70BM (1 : 1, w/w) reached 6.03% with a Jsc of 12.46 mA cm−2, a Voc of 0.78 V and a FF of 0.62, while PBDTT–DTBT/PC70BM (1 : 1, w/w) only has a PCE of 2.34% with a Voc of 0.82 V, a Jsc of 5.78 mA cm−2 and a FF of 0.495 under the illumination of AM 1.5 G, 100 mW cm−2. These results indicate that PBDTT–DTTBT is a promising photovoltaic material. Furthermore, it can be concluded that extending the conjugation of the backbone units, as demonstrated in this work, has little influence on the molecular energy levels, but can be seen as a feasible strategy to improve the photovoltaic properties of D–π–A conjugated polymers by enhancing intermolecular interactions.

  。
• Synthesis and photovoltaic properties of D-π-A copolymers based on thieno[3,2-b]thiophene bridge unit
  作者：Zhaojun Li、Lijun Huo、Xia Guo、Weina Yong、Shaoqing Zhang、Huili Fan

  DOI：10.1016/j.polymer.2013.09.021

  日期：2013.10

  Three D-pi-A copolymers containing thieno[3,2-b]thiophene (TT) bridge and BDT, carbazole, fluorene as D units and benzothiadiazole as A unit were synthesized and characterized. These copolymers of PBDT-tt-BT, PC-tt-BT and PF-tt-BT exhibited enough high thermal stabilites and good solubilites in chloroform and dichlorobenzene. Among the copolymers, with the increase of the electron-donating abilities of the D units from fluorene to carbazole further to BDT, the absorption spectra of PF-tt-BT shows blue shift and that of PBDT-tt-BT shows red shift comparing to that of PC-tt-BT in their solutions and films. Meanwhile, by electrochemical cyclic voltammetry measurements we found the HOMO levels vary in the same trench according to their electron-donating abilities. Under the illumination of AM 1.5G, 100 mW/cm(2), power conversion efficiency (PCE) of the PSCs based on these copolymers as donors and PC70M as acceptor were measured and PBDT-tt-BT shows a higher efficiency of 4.91% than PC-tt-ST and PF-tt-BT based devices mostly due to its higher hole mobility and broader absorption range. These results indicate that PBDT-tt-BT is a promising photovoltaic polymer donor material for efficient PSCs. (C) 2013 Elsevier Ltd. All rights reserved.
• The Combination of S⋯N and S⋯Cl Noncovalently Conformational Locks for Constructing <scp>High‐Planarity</scp> and <scp>Low‐Cost Nonfused‐Ring</scp> Electron Acceptors†
  作者：Ziyang Han、Congqi Li、Xiaobin Gu、Xiao Han、Sixuan Wang、Yanan Wei、Jinhua Gao、Zhixiang Wei、Yunhao Cai、Xin Zhang、Hui Huang

  DOI：10.1002/cjoc.202300006

  日期：——

  units, two A-D-A′-D-A type nonfused-ring electron acceptors (NFREAs) Tz-H and Tz-Cl were designed and synthesized. Replacing thiazole in Tz-H with 4-chlorothiazole can not only remarkably shorten the synthetic route through C—H direct arylation but also enhance molecular planarity with the simultaneous incorporation of S···N and S···Cl noncovalently conformational locks (NoCLs). The photovoltaic devices

  以噻唑和4-氯噻唑为A'单元，设计并合成了两种ADA'-DA型非稠环电子受体（NFREA）Tz-H和Tz-Cl 。用4-氯噻唑取代Tz-H中的噻唑不仅可以显着缩短C—H直接芳基化的合成路线，而且可以通过同时掺入S·N和S·Cl非共价构象锁来增强分子平面性（NoCLs ））。基于PM6: Tz-Cl的光伏器件的电能转换效率高达11.10%，远高于PM6: Tz-H（6.41%），主要是由于更有效的激子解离、更好且更平衡的载流子迁移率、更少的电荷复合以及更有利的形貌。这些发现证明了 NoCL 在实现低成本和高性能 NFREA 方面的巨大潜力。