2-(5'-bromo-2,2'-bithiophen-5-yl)-5,5-dimethyl-1,3-dioxane | 1372699-62-1

• 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)-5,5-dimethyl-1,3-dioxane
• 英文别名: 2-[5-(5-Bromothiophen-2-yl)thiophen-2-yl]-5,5-dimethyl-1,3-dioxane
• CAS: 1372699-62-1
• 化学式: C₁₄H₁₅BrO₂S₂
• 分子量: 359.308
• InChiKey: GTGZGPVIWQRHEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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)-5,5-dimethyl-1,3-dioxane 在 四(三苯基膦)钯 、 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 27.0h， 生成 5'-(4-(二苯氨基)苯基)-[2,2'-联噻吩]-5-甲醛
  参考文献：
  名称：

  Dye / TiO2 / Pt杂化体系中可见光氢演化的亲水性控制和电荷分离态的动力学

  摘要：

  研究了基于染料/ TiO 2 / Pt杂化光催化剂的可见光驱动的H 2演化，用于一系列（E）-3-（5′-{4- [bis（4-R 1-苯基）氨基]苯基} -4,4' - （R 2）2 -2,2'-联噻吩-5-基）-2-氰基丙烯酸染料。发现在乙二胺四乙酸作为电子供体的情况下，在λ > 420 nm的光照下，从水性悬浮液中析出的氢的效率很大程度上取决于R 1的亲水特性，其变化顺序为MOD（R 1 = CH 3 OCH 2， R 2 = H）≈MO4D（R 1＝ R 2＝ CH 3 OCH 2）＞HD（R 1＝ R 2＝ H）＞PD（R 1＝ C 3 H 7，R 2＝ H）。在MOD / TiO 2 / Pt的情况下，在436nm处光催化的H 2产生的表观量子产率为0.27±0.03。对MOD-或PD接枝的TiO 2纳米颗粒透明膜浸入pH为3的水中进行瞬态吸收测量，通常显示染料自由基阳离子（Dye

  DOI：

  10.1002/chem.201201500
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联噻吩 在 正丁基锂 、 对甲苯磺酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 2-(5'-bromo-2,2'-bithiophen-5-yl)-5,5-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Dye / TiO2 / Pt杂化体系中可见光氢演化的亲水性控制和电荷分离态的动力学

  摘要：

  研究了基于染料/ TiO 2 / Pt杂化光催化剂的可见光驱动的H 2演化，用于一系列（E）-3-（5′-{4- [bis（4-R 1-苯基）氨基]苯基} -4,4' - （R 2）2 -2,2'-联噻吩-5-基）-2-氰基丙烯酸染料。发现在乙二胺四乙酸作为电子供体的情况下，在λ > 420 nm的光照下，从水性悬浮液中析出的氢的效率很大程度上取决于R 1的亲水特性，其变化顺序为MOD（R 1 = CH 3 OCH 2， R 2 = H）≈MO4D（R 1＝ R 2＝ CH 3 OCH 2）＞HD（R 1＝ R 2＝ H）＞PD（R 1＝ C 3 H 7，R 2＝ H）。在MOD / TiO 2 / Pt的情况下，在436nm处光催化的H 2产生的表观量子产率为0.27±0.03。对MOD-或PD接枝的TiO 2纳米颗粒透明膜浸入pH为3的水中进行瞬态吸收测量，通常显示染料自由基阳离子（Dye

  DOI：

  10.1002/chem.201201500

文献信息

• Control of Electron Transfer Processes in Multidimensional Arylamine-Based Mixed-Valence Compounds by Molecular Backbone Design
  作者：Agostina-L. Capodilupo、Eduardo Fabiano、Lorenzo Franco、Salvatore Gambino、Mauro Leoncini、Gianluca Accorsi、Giuseppe Gigli

  DOI：10.1021/acs.jpca.1c05435

  日期：2021.9.16

  Four trigonal topology compounds with three diarylamines redox centers and dibenzofulvene as core bridge have been synthesized. Their radical cations exhibit appealing intramolecular electron transfer pathways between three redox centers, depending on their position on the core bridge. By changing such positions (on either 2,7- or 3,6-), and the length of the bridge, the control of the intramolecular

  合成了四种具有三个二芳胺氧化还原中心和二苯并富烯作为核心桥的三角拓扑化合物。它们的自由基阳离子在三个氧化还原中心之间表现出吸引人的分子内电子转移途径，这取决于它们在核心桥上的位置。通过改变这些位置（在 2,7- 或 3,6- 上）和桥的长度，通过电子自交换途径实现了对分子内电子转移途径的控制。通过吸收光谱、电子顺磁共振光谱和（时间相关）密度泛函理论计算研究了这些过程。还进行了空穴迁移率测量，以将分子内电子转移与光电器件中可能应用的空穴传输能力相关联。
• [EN] NOVEL OLIGOTHIOPHENE DERIVATIVES, THEIR PROCESS OF PREPARATION AND THEIR USES<br/>[FR] NOUVEAUX DÉRIVÉS OLIGOTHIOPHÈNES, LEURS PROCÉDÉS DE PRÉPARATION ET LEURS UTILISATIONS
  申请人：UNIV AIX MARSEILLE II

  公开号：WO2012049167A1

  公开（公告）日：2012-04-19

  The present invention concerns novel oligothiophene derivatives bearing reactive functions, their process of preparation, their use for preparing electrically semi-conducting organic compounds, their preparation thereof and nanohybrid nanocomposite material containing them.

  本发明涉及具有反应性功能的新型寡噻吩衍生物，它们的制备过程，用于制备半导电有机化合物的用途，它们的制备方法以及含有它们的纳米混合纳米复合材料。
• Donor-π-Acceptor Type Diphenylaminothiophenyl Anthracene-mediated Organic Photosensitizers for Dye-sensitized Solar Cells
  作者：Dong Uk Heo、Sun Jae Kim、Beom Jin Yoo、Boeun Kim、Min Jae Ko、Min Ju Cho、Dong Hoon Choi

  DOI：10.5012/bkcs.2013.34.4.1081

  日期：2013.4.20

  Two new metal-free organic dyes bridged by anthracene-mediated $\pi}$-conjugated moieties were successfully synthesized for use in a dye-sensitized solar cell (DSSC). A N,N-diphenylthiophen-2-amine unit in these dyes acts as an electron donor, while a (E)-2-cyano-3-(thiophen-2-yl)acrylic acid group acts as an electron acceptor and an anchoring group to the $TiO_2$ electrode. The photovoltaic properties of (E)-2-cyano-3-(5-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)thiophen-2-yl)acrylic acid (DPATAT) and (E)-2-cyano-3-(5'-((10-(5-(diphenylamino)thiophen-2-yl)anthracen-9-yl)ethynyl)-2,2'-bithiophen-5-yl)acrylic acid (DPATABT) were investigated to identify the effect of conjugation length between electron donor and acceptor on the DSSC performance. By introducing an anthracene moiety into the dye structure, together with a triple bond and thiophene moieties for fine-tuning of molecular configurations and for broadening the absorption spectra, the short-circuit photocurrent densities ($J_sc}$), and open-circuit photovoltages ($V_oc}$) of DSSCs were improved. The improvement of $J_sc}$ in DSSC made of DPATABT might be attributed to much broader absorption spectrum and higher molecular extinction coefficient ($\varepsilon}$) in the visible wavelength range. The DPATABT-based DSSC showed the highest power conversion efficiency (PCE) of 3.34% ($\eta}_max}$ = 3.70%) under AM 1.5 illumination ($100mWcm^-2}$) in a photoactive area of $0.41cm^2$, with the $J_sc}$ of $7.89mAcm^-2}$, the $V_oc}$ of 0.59 V, and the fill factor (FF) of 72%. In brief, the solar cell performance with DPATABT was found to be better than that of DPATAT-based DSSC.

  34%)。
• Chemically Altering the Solubility and Durability of Dyes for Sensitized Solar Cells
  作者：Subashani Maniam、Andrew B. Holmes、Gary A. Leeke、Ante Bilic、Gavin E. Collis

  DOI：10.1021/acs.orglett.5b01921

  日期：2015.8.21

  By designing dyes with fluoroalkyl groups, the optical and electronic properties of the alkyl analogue were maintained while dramatically altering the solubility. Dyes, F-TABTA (8) and its masked derivative F-TABTSi (9), that enable them to be deposited under conventional organic solvent and scCO(2) conditions, respectively, were developed, hi liquid DSSC devices, the fluoroalkyl dye (F-TABTA, 8) performs slightly better than its alkyl analogue (D21L6, 10), and interestingly, it was found that the former device showed better stability over time. Deploying the silyl-masked precursor F-TABTSi (9), this dye was deposited onto TiO2 photoanodes from scCO(2) in very short contact times (2.5 h), and ECEs of 7.70% were obtained that exceed the performance of the alkyl dye when deposited by conventional methods.