3-bromo-10-butyl-10H-phenothiazine | 914251-88-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-bromo-10-butyl-10H-phenothiazine
• 英文别名: 3-Bromo-10-butylphenothiazine
• CAS: 914251-88-0
• 化学式: C₁₆H₁₆BrNS
• 分子量: 334.28
• InChiKey: ZUQBNCLXYXWDHN-UHFFFAOYSA-N

物化性质

• 沸点：
  433.2±44.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-10-butyl-10H-phenothiazine 在 哌啶 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 3-(5-(10-butyl-10H-phenothiazin-3-yl)thiophen-2-yl)-2-cyanoacrylic acid
  参考文献：
  名称：

  Effect of Five-Membered Heteroaromatic Linkers to the Performance of Phenothiazine-Based Dye-Sensitized Solar Cells

  摘要：

  Phenothiazine derivatives with various conjugated linkers (furan, thiophene, and 3,4-ethylenedioxythiophene) were synthesized and used in dye-sensitized solar cells to study the effect of conjugated linkers on device performance. Among them, one with furan as a conjugated linker showed a solar energy-to-electricity conversion efficiency (eta) of 6.58%, an improvement of over 24% compared with the T2-1 reference cells' 5.29% under AM 1.5 G irradiation.

  DOI：

  10.1021/ol2023517
• 作为产物：
  描述：

  吩噻嗪 在 N-溴代丁二酰亚胺(NBS) 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.17h， 生成 3-bromo-10-butyl-10H-phenothiazine
  参考文献：
  名称：

  Spin–orbit charge transfer intersystem crossing in perylenemonoimide–phenothiazine compact electron donor–acceptor dyads

  摘要：

  基于自旋轨道电荷转移ISC，观察到基于苝单亚胺-苯噻嗪紧凑电子给体-受体二聚体的高效三重激发态产生（57%）。

  DOI：

  10.1039/c8cc07012a

文献信息

• Phenothiazine derivatives-based D–π–A and D–A–π–A organic dyes for dye-sensitized solar cells
  作者：Xichuan Yang、Jianghua Zhao、Lei Wang、Jie Tian、Licheng Sun

  DOI：10.1039/c4ra01858c

  日期：——

  D–π–A and D–A–π–A-structured organic dyes represent different developmental directions of photosensitizers in dye-sensitized solar cells (DSSCs). In this work, two phenothiazine derivatives-based D–π–A and D–A–π–A-structured organic dyes have been synthesized and applied in DSSCs. The physical and electrochemical properties of both dyes have been investigated systematically. The results show that the D–A–π–A-structured dye exhibits a broader spectrum response but lower molar coefficient of extinction when compared to the D–π–A-structured dye. Regarding photovoltaic performance, the D–π–A-structured dye yields a higher efficiency (η) of 7.5% with a higher short-circuit current density (Jsc) of 16.36 mA cm−2 and open-circuit voltage (Voc) of 706 mV than that of the D–A–π–A-structured dye. Incident photon-to-electron conversion efficiency (IPCE) studies and impedance analysis also support these results. These results demonstrate that the phenothiazine derivatives-based D–π–A-structured organic dyes can compete with, and even exceed, D–A–π–A-structured organic dyes under the same test conditions.

  D–π–A 和 D–A–π–A 型有机染料代表了染料敏化太阳能电池 (DSSCs) 中光敏剂的不同发展方向。在这项工作中，合成了两种基于吩噻嗪衍生物的 D–π–A 和 D–A–π–A 型有机染料，并应用于 DSSCs 中。系统研究了两种染料的物理和电化学性质。结果表明，与 D–π–A 型染料相比，D–A–π–A 型染料具有更宽的光谱响应，但摩尔消光系数较低。在光伏性能方面，D–π–A 型染料的效率 (η) 为 7.5%，短路电流密度 (Jsc) 为 16.36 mA cm−2，开路电压 (Voc )为706 mV，优于D–A–π–A型染料。入射光子-电子转换效率 (IPCE) 研究和阻抗分析也支持这些结果。这些结果表明，在相同的测试条件下，基于吩噻嗪衍生物的 D–π–A 型有机染料可以与 D–A–π–A 型有机染料竞争，甚至超过后者。
• Molecular Design of D-π-A Type II Organic Sensitizers for Dye Sensitized Solar Cells
  作者：Shifeng Li、Xichuan Yang、Dingfeng Qu、Weihan Wang、Yu Wang、Licheng Sun

  DOI：10.1002/cjoc.201200758

  日期：2012.10

  Four new type II organic dyes with D‐π‐A structure (donor‐π‐conjugated‐acceptor) and two typical type II sensitizers based on catechol as reference dyes are synthesized and applied in dye sensitized solar cells (DSCs). The four dyes can be adsorbed on TiO2 through hydroxyl group directly. Electron injection can occur not only through the anchoring group (hydroxyl group) but also through the electron‐withdrawing

  合成了四种具有D-π-A结构的新型II型有机染料（供体-π-共轭受体）和两种基于儿茶酚的典型II型敏化剂作为参考染料，并将其应用于染料敏化太阳能电池（DSC）。四种染料可以直接通过羟基吸附在TiO 2上。电子注入不仅可以通过锚定基团（羟基）发生，而且可以通过靠近半导体表面的吸电子基团（CN）发生。实验结果表明，具有D-π-A系统的II型敏化剂明显优于典型的II型敏化剂，由于其强大的电子推挽效应，后者可提供更高的转化效率。在这些染料中，LS223给出最佳的太阳能转换效率为3.6％，当J sc = 7.3 mA·cm -2，V oc = 0.69 V，FF = 0.71时，最大IPCE值达到74.9％。
• Triplet Excited State of BODIPY Accessed by Charge Recombination and Its Application in Triplet–Triplet Annihilation Upconversion
  作者：Kepeng Chen、Wenbo Yang、Zhijia Wang、Alessandro Iagatti、Laura Bussotti、Paolo Foggi、Wei Ji、Jianzhang Zhao、Mariangela Di Donato

  DOI：10.1021/acs.jpca.7b07623

  日期：2017.10.12

  The triplet excited state properties of two BODIPY phenothiazine dyads (BDP-1 and BDP-2) with different lengths of linker and orientations of the components were studied. The triplet state formation of BODIPY chromophore was achieved via photoinduced electron transfer (PET) and charge recombination (CR). BDP-1 has a longer linker between the phenothiazine and the BODIPY chromophore than BDP-2. Moreover

  研究了两个BODIPY吩噻嗪二联体（BDP-1和BDP-2）在不同的连接体长度和组分的取向下的三重激发态性质。BODIPY发色团的三重态形成是通过光致电子转移（PET）和电荷重组（CR）实现的。BDP-1具有吩噻嗪和BODIPY发色团比之间的较长接头BDP-2 。此外，BDP-2中的两个发色团在地面和第一激发态（87°）处都比BDP-1具有更正交的几何形状（34–40°）。BODIPY部分的荧光在二倍体中被显着淬灭。飞秒瞬态吸收光谱法研究了二元组的电荷分离（CS）和CR动力学（对于BDP-1和BDP-2，k CS分别为2.2×10 11 s –1和2×10 12 s –1；k对于BDP-1和BDP-2，CR = 4.5×10 10和1.5×10 11 s –1， 分别; 在乙腈中）。在光激发下，对于两个二元组都观察到BODIPY部分的三重态激发态的形成，并且三重态量子产率取决于接头长度和发
• PORPHYRIN PHOTOSENSITIVE DYE AND PHOTOELECTRIC CONVERSION DEVICE UTILIZING THE SAME
  申请人：Industrial Technology Research Institute

  公开号：US20160009921A1

  公开（公告）日：2016-01-14

  Disclosed is a porphyrin photosensitive dye, having the chemical formula: Each of L 1 and L 2 is independently R 1 is C 5-20 linear/branched alkyl group. R 2 is C 0-20 linear/branched alkyl group. R 4 is C 1-20 linear/branched alkyl group. Each of R 3 and R 5 is independently C 1-20 linear/branched i alkyl group or C 1-20 linear/branched alkoxy group. Y 1 is C 3-20 cycloalkyl group. Each of a and b is independently an integer of 0 to 5. D is Each of R 6 to R 11 is independently C 1-10 alkyl group. X 1 is N, O, S, or Se. Each of c, d, and e is independently an integer of 0 to 5. A is Each of Z 1 and Z 2 is independently hydrogen, alkali metal, or quaternary ammonium salt —N(R 12 ) 4 . R 12 is C 1-10 alkyl group. X 2 is N, O, S, or Se.

  揭示了一种卟啉光敏染料，其化学式为：L1和L2中的每一个独立取值为R1是C5-20直链/支链烷基基团。R2是C0-20直链/支链烷基基团。R4是C1-20直链/支链烷基基团。R3和R5中的每一个独立取值为C1-20直链/支链烷基基团或C1-20直链/支链烷氧基团。Y1是C3-20环烷基团。a和b中的每一个独立取值为0到5的整数。D是R6到R11中的每一个独立取值为C1-10烷基基团。X1是N、O、S或Se。c、d和e中的每一个独立取值为0到5的整数。A是Z1和Z2中的每一个独立取值为氢、碱金属或季铵盐—N(R12)4。R12是C1-10烷基基团。X2是N、O、S或Se。
• Improving the electroluminescence performance of donor–acceptor molecules by fine-tuning the torsion angle and distance between donor and acceptor moieties
  作者：Xu Qiu、Shanfeng Xue、Yongjin Wu、Mingshuai Chen、Qikun Sun、Wenjun Yang

  DOI：10.1039/c6tc01269h

  日期：——

  designed and synthesized to tune the torsion angle and distance between D and A moieties, and their photophysical and electroluminescence properties were investigated. The D–A type molecule PO has a planar conformation, whereas the D–π–A type molecule PPO has a twisted conformation because of the insertion of the phenyl bridge between the donor and the acceptor. Therefore, the charge transfer (CT) of PPO

  供体（D）和受体（A）之间的扭转角和距离是确定扭曲的D–A型有机分子的光致发光和电致发光性质的两个重要因素。在这里，有两种新的D–A化合物，2-（10-丁基-10 H-吩噻嗪-3-基）-5-苯基-1,3,4-恶二唑（PO）和2-（4-（10-丁基-10小时设计并合成了-吩噻嗪-3-基）苯基）-5-苯基-1,3,4-恶二唑（PPO），以调节D和A部分之间的扭转角和距离，并研究了它们的光物理和电致发光性质。D–A–型分子PO具有平面构象，而D–π–A型分子PPO具有扭曲的构象，这是因为在供体和受体之间插入了苯基桥。因此，PPO的电荷转移（CT）比PO的电荷转移要强得多，并且PPO的单重态激子产率可能比PO高。在另一方面，引入了苯基的单元也可以提高光致发光量子效率（掺杂膜Φ PL≈70％）。结果，掺杂PPO的设备显示出比PO更好的设备性能。基于PPO作为发射器的器件表现出稳定且高的发光效率（15