4-hexylthiophene-2-boronic acid 2,2-dimethyl-1,3-propanedioxide ester | 205105-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: 4-hexylthiophene-2-boronic acid 2,2-dimethyl-1,3-propanedioxide ester
• 英文别名: 5,5-dimethyl-2-(4-octylthien-2-yl)[1,3,2]dioxaborinane；5,5-Dimethyl-2-(4-octylthiophen-2-YL)-1,3,2-dioxaborinane；5,5-dimethyl-2-(4-octylthiophen-2-yl)-1,3,2-dioxaborinane
• CAS: 205105-15-3
• 化学式: C₁₇H₂₉BO₂S
• 分子量: 308.293
• InChiKey: UIPUPVHBVAILFB-UHFFFAOYSA-N

物化性质

• 沸点：
  417.1±33.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.42
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hexylthiophene-2-boronic acid 2,2-dimethyl-1,3-propanedioxide ester 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,7-bis(5-bromo-4-octylthien-2-yl)-fluoren-9-one
  参考文献：
  名称：

  Regiochemically Well-Defined Fluorenone−Alkylthiophene Copolymers:  Synthesis, Spectroscopic Characterization, and Their Postfunctionalization with Oligoaniline

  摘要：

  A new solution processable, regioregular, alternate copolymer of fluorenone and dialkyl-bithiophene, namely poly [(5,5'-(3,3'-di-n-octyl-2,2'-bithiophene))-alt-(2,7-fluoren-9-one)] (abbreviated as PDOBTF), was synthesized by three different preparation methods: chemical or electrochemical oxidation of 2,7-bis(4-octylthien-2-yl)-fluoren-9-one or polycondensation of 2,7-bis(5-bromo-4-octylthien-2-yl)-fluoren-9-one in the presence of Ni(0) reagent. Independent of the preparation method, the crude product is a mixture of high molecular weight fractions and short oligomers. It can be however easily fractionated into fractions differing in their molecular weight by sequential extractions with a series of solvents. The principal absorption band registered for the undoped polymer (lambda(max) = 384 nm for the THF solution and 389 nm for the solid state) originates from the pi-->pi* transition of the conjugated backbone and is blue-shifted because of the chain torsion effects caused by steric hindrance. This band is accompanied by a peak of smaller intensity (lambda(max) = 476 nm for the THF solution and 485 nm for the solid state) attributed to the n-pi* transition in the carbonyl group of the fluoren-9-one subunit. Preliminary photoluminescence studies show that PDOBTF exhibits a very large Stokes shift and emits red light (lambda(max) = 631 nm in THF solution and 643 nm in the solid state). Upon chemical p-type doping with FeCl4-, the polymer reaches the conductivity of sigma(dc) = 0.05 S cm(-1). Mossbauer spectroscopy studies of the doping process show that both structural subunits, i.e., the bithiophene subunit and the fluoren-9-one one, participate in the doping. PDOBTF can be relatively easily postfunctionalized by grafting aniline oligomers as pendant groups via the carbonyl groups of the fluoren-9-one subunit. By consequence, the spectrum of the modified polymer can be precisely tuned in the visible region by changing the grafting level.

  DOI：

  10.1021/ma030171z
• 作为产物：
  描述：

  硼酸三甲酯 、 3-辛基噻吩 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以83%的产率得到4-hexylthiophene-2-boronic acid 2,2-dimethyl-1,3-propanedioxide ester
  参考文献：
  名称：

  Development of Novel n-Type Materials Based on Benzothiadiazole Derivatives for Organic Photovoltaics: Effects of Acceptor Terminal Substituents

  摘要：

  合成了新型n型材料BTD-CN（1）和BTD-CF3（2）用于有机光伏。两种材料的HOMO-LUMO能级和吸收峰位置大致相同。然而，使用1的器件的有机光伏性能明显高于使用2的器件。在本文中，我们讨论了末端取代基对薄膜形态、结晶性和光伏性能的影响。结果表明，氰基改性的苯并噻二唑由于其结晶性、载流子复合和串联电阻而具有实用价值。

  DOI：

  10.1246/cl.141155

文献信息

• Effect of substituents on redox, spectroscopic and structural properties of conjugated diaryltetrazines—a combined experimental and theoretical study
  作者：Ewa Kurach、David Djurado、Jan Rimarčik、Aleksandra Kornet、Marek Wlostowski、Vladimir Lukeš、Jacques Pécaut、Malgorzata Zagorska、Adam Pron

  DOI：10.1039/c0cp01553a

  日期：——

  alkylthienyl, phenyl or pyridyl) with hydrazine followed by oxidation of the intermediate product with diethyl azodicarboxylate. The five-ring compounds have been prepared using two pathways: (i) reaction of 5-cyano-2,2′-bithiophene (or its alkyl derivative) with hydrazine; (ii) via Suzuki or Stille coupling of 3,6-bis(5-bromo-2-thienyl)-1,2,4,5-tetrazine with a stannyl or boronate derivative of alkylthiophene

  两套新的可溶性共轭化合物 四嗪中心环已合成。三环化合物是通过芳基反应合成的氰化物 （其中芳基= 噻吩基，烷基噻吩基，苯基或吡啶基）与 肼 然后用 偶氮二羧酸二乙酯。五环化合物已通过两种途径制备：（i）5-氰基-2,2'-联噻吩 （或其烷基衍生物）与 肼; （ii）通过Suzuki或Stille联轴器3,6-双（5-溴-2-噻吩基）-1,2,4,5-四嗪 与斯坦尼或 硼酸盐烷基噻吩的衍生物。紫外-可见的合成的化合物的光谱性质强烈地依赖于该芳基，增溶取代基的位置和该分子的长度，显示出最高红移的性质（λ最大> 440纳米）为5环化合物用烷基连接到C α 碳 在终端 噻吩基戒指。已经找到了极好的线性相关性，可用于光谱测定和理论计算（TD-B3LYP/ 6-31G *）激发能量。除了双吡啶导数，根据电化学数据，所研究分子的最低未占据分子轨道（LUMO）水平在狭窄范围内变化（从-2.63至-2.41
• ORGANIC COLOURANT AND USES THEREOF IN PHOTOVOLTAIC CELLS
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：US20140290748A1

  公开（公告）日：2014-10-02

  The present invention relates to an organic colorant corresponding to one of the following structures (I) or (II): eD-pi-conjugated chromophore-L-A  (I) A-L-pi-conjugated chromophore-eD  (II) in which eD represents an electron donor segment; L represents a covalent bond or a spacer segment; A represents an electron attractor segment able to form a covalent bond with a semi-conductor; the pi-conjugated chromophore comprising at least two aromatic rings, at least one of which is a thiophene, selenophene or furan type ring. The present invention relates to the use thereof as photosensitizer in a photovoltaic device and said photovoltaic device.

  本发明涉及与以下结构（I）或（II）之一相对应的有机染料： eD-π-共轭色团-L-A  （I） A-L-π-共轭色团-eD  （II） 其中，eD代表电子给体片段；L代表共价键或间隔片段；A代表能够与半导体形成共价键的电子吸引片段；π-共轭色团包括至少两个芳香环，其中至少一个是噻吩、硒吩或呋喃型环。本发明涉及将其用作光伏器件中的光敏剂以及该光伏器件。
• Organic colourant and uses thereof in photovoltaic cells
  申请人：COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES

  公开号：US09171676B2

  公开（公告）日：2015-10-27

  The present invention relates to an organic colorant corresponding to one of the following structures (I) or (II): eD-pi-conjugated chromophore-L-A  (I) A-L-pi-conjugated chromophore-eD  (II) in which eD represents an electron donor segment; L represents a covalent bond or a spacer segment; A represents an electron attractor segment able to form a covalent bond with a semi-conductor; the pi-conjugated chromophore comprising at least two aromatic rings, at least one of which is a thiophene, selenophene or furan type ring. The present invention relates to the use thereof as photosensitizer in a photovoltaic device and said photovoltaic device.

  本发明涉及与以下结构（I）或（II）之一对应的有机染料：eD-π-共轭色团-L-A  （I）A-L-π-共轭色团-eD  （II）其中，eD代表电子供体段；L代表共价键或空间段；A代表能够与半导体形成共价键的电子吸引体段；π-共轭色团包括至少两个芳香环，其中至少一个是噻吩、硒吩或呋喃型环。本发明涉及将其用作光伏器件中的光敏剂及该光伏器件。
• Development of Novel n-Type Materials Based on Benzothiadiazole Derivatives for Organic Photovoltaics: Effects of Acceptor Terminal Substituents
  作者：Yosei Shibata、Takahiro Kono、Hiroyo Usui、Yuji Yoshida

  DOI：10.1246/cl.141155

  日期：2015.5.5

  Novel n-type materials of BTD-CN (1) and BTD-CF3 (2) were synthesized for organic photovoltaics. Both materials show approximately the same HOMO–LUMO level and position of absorption peaks. However, the organic photovoltaic performance of a device with 1 is clearly higher than that with 2. In this paper, we discuss the effects of terminal substituents on film morphology, crystallinity, and photovoltaic performance. The results suggest that cyano-modified benzothiadiazole is useful because of its crystallinity, carrier recombination, and series resistance.

  合成了新型n型材料BTD-CN（1）和BTD-CF3（2）用于有机光伏。两种材料的HOMO-LUMO能级和吸收峰位置大致相同。然而，使用1的器件的有机光伏性能明显高于使用2的器件。在本文中，我们讨论了末端取代基对薄膜形态、结晶性和光伏性能的影响。结果表明，氰基改性的苯并噻二唑由于其结晶性、载流子复合和串联电阻而具有实用价值。
• Regiochemically Well-Defined Fluorenone−Alkylthiophene Copolymers:  Synthesis, Spectroscopic Characterization, and Their Postfunctionalization with Oligoaniline
  作者：Renaud Demadrille、Patrice Rannou、Joël Bleuse、Jean-Louis Oddou、Adam Pron、Malgorzata Zagorska

  DOI：10.1021/ma030171z

  日期：2003.9.1

  A new solution processable, regioregular, alternate copolymer of fluorenone and dialkyl-bithiophene, namely poly [(5,5'-(3,3'-di-n-octyl-2,2'-bithiophene))-alt-(2,7-fluoren-9-one)] (abbreviated as PDOBTF), was synthesized by three different preparation methods: chemical or electrochemical oxidation of 2,7-bis(4-octylthien-2-yl)-fluoren-9-one or polycondensation of 2,7-bis(5-bromo-4-octylthien-2-yl)-fluoren-9-one in the presence of Ni(0) reagent. Independent of the preparation method, the crude product is a mixture of high molecular weight fractions and short oligomers. It can be however easily fractionated into fractions differing in their molecular weight by sequential extractions with a series of solvents. The principal absorption band registered for the undoped polymer (lambda(max) = 384 nm for the THF solution and 389 nm for the solid state) originates from the pi-->pi* transition of the conjugated backbone and is blue-shifted because of the chain torsion effects caused by steric hindrance. This band is accompanied by a peak of smaller intensity (lambda(max) = 476 nm for the THF solution and 485 nm for the solid state) attributed to the n-pi* transition in the carbonyl group of the fluoren-9-one subunit. Preliminary photoluminescence studies show that PDOBTF exhibits a very large Stokes shift and emits red light (lambda(max) = 631 nm in THF solution and 643 nm in the solid state). Upon chemical p-type doping with FeCl4-, the polymer reaches the conductivity of sigma(dc) = 0.05 S cm(-1). Mossbauer spectroscopy studies of the doping process show that both structural subunits, i.e., the bithiophene subunit and the fluoren-9-one one, participate in the doping. PDOBTF can be relatively easily postfunctionalized by grafting aniline oligomers as pendant groups via the carbonyl groups of the fluoren-9-one subunit. By consequence, the spectrum of the modified polymer can be precisely tuned in the visible region by changing the grafting level.