4,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazole | 1619232-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-bis(5-ethynyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazole
• CAS: 1619232-20-0
• 化学式: C₃₀H₃₂N₂S₃
• 分子量: 516.795
• InChiKey: YVDKBGAOWCTVAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氯(三甲基膦)金 、 4,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazole 在 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 0.5h， 以67%的产率得到
  参考文献：
  名称：

  Photophysics and Nonlinear Absorption of Gold(I) and Platinum(II) Donor–Acceptor–Donor Chromophores

  摘要：

  A series of Au(I) and Pt(II) acetylide complexes of a Itconjugated donor-acceptor-donor (D-A-D) chromophore were studied to develop quantitative structure property relationships for their photophysical and nonlinear optical properties. The D-A-D chromophore consists of a "TBT" unit, where T = 3-hexyl-2,5-thienylene and BTD = 2,1,3-benzothiadiazole, capped with ethynylene groups. The D-A-D chromophore is functionalized with Au(I)PR3 (R = -Me and -Ph) and trans-Pt(II)(PR3)(2)-CCPh (R = -Me and -Bu) auxochromes". All of the metal complexes were characterized by ground-state absorption, photoluminescence, nanosecond transient absorption, and two-photon absorption (2PA) spectroscopy. The experiments provided quantitative values of the photophysical parameters, including rates for radiative decay and intersystem crossing (ISC), triplet yields, and two-photon absorption cross sections. Pronounced solvatochromism in the fluorescence spectra suggests an enhanced dipole moment in the excited state of the complexes compared to the unmetalated TBT chromophore. The gold complexes feature larger fluorescence quantum yields and longer emission lifetimes compared to platinum. The Pt(II) complexes exhibit enhanced triplet triplet absorption, reduced triplet-state lifetimes, and larger singlet oxygen quantum yields, consistent with more efficient ISC compared to the Au(I) complexes. When excited by 100 fs pulses, all of the D-A-D chromophores exhibit moderate two-photon absorption in the near-infrared between 700 and 900 nm. The 2PA cross section for the Au(I) complexes is almost the same as the unmetalated D-A-D chromophore (similar to 100 GM). The Pt(II) complexes exhibit significantly enhanced 2PA compared to the other chromophores, reaching 1000 GM at 750 nm. Taken together, the results indicate that the Pt(II) center is considerably more effective in inducing singlet-triplet ISC and in enhancing the 2PA cross section. This result reveals the greater promise for Pt(II) acetylides in chromophores for temporal and frequency agile nonlinear absorption.

  DOI：

  10.1021/acs.inorgchem.5b01767
• 作为产物：
  描述：

  4,7-双(4-己基噻吩基)苯并[C][1,2,5]噻二唑 在 哌啶 、 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 4.5h， 生成 4,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Photophysics and Nonlinear Absorption of Gold(I) and Platinum(II) Donor–Acceptor–Donor Chromophores

  摘要：

  A series of Au(I) and Pt(II) acetylide complexes of a Itconjugated donor-acceptor-donor (D-A-D) chromophore were studied to develop quantitative structure property relationships for their photophysical and nonlinear optical properties. The D-A-D chromophore consists of a "TBT" unit, where T = 3-hexyl-2,5-thienylene and BTD = 2,1,3-benzothiadiazole, capped with ethynylene groups. The D-A-D chromophore is functionalized with Au(I)PR3 (R = -Me and -Ph) and trans-Pt(II)(PR3)(2)-CCPh (R = -Me and -Bu) auxochromes". All of the metal complexes were characterized by ground-state absorption, photoluminescence, nanosecond transient absorption, and two-photon absorption (2PA) spectroscopy. The experiments provided quantitative values of the photophysical parameters, including rates for radiative decay and intersystem crossing (ISC), triplet yields, and two-photon absorption cross sections. Pronounced solvatochromism in the fluorescence spectra suggests an enhanced dipole moment in the excited state of the complexes compared to the unmetalated TBT chromophore. The gold complexes feature larger fluorescence quantum yields and longer emission lifetimes compared to platinum. The Pt(II) complexes exhibit enhanced triplet triplet absorption, reduced triplet-state lifetimes, and larger singlet oxygen quantum yields, consistent with more efficient ISC compared to the Au(I) complexes. When excited by 100 fs pulses, all of the D-A-D chromophores exhibit moderate two-photon absorption in the near-infrared between 700 and 900 nm. The 2PA cross section for the Au(I) complexes is almost the same as the unmetalated D-A-D chromophore (similar to 100 GM). The Pt(II) complexes exhibit significantly enhanced 2PA compared to the other chromophores, reaching 1000 GM at 750 nm. Taken together, the results indicate that the Pt(II) center is considerably more effective in inducing singlet-triplet ISC and in enhancing the 2PA cross section. This result reveals the greater promise for Pt(II) acetylides in chromophores for temporal and frequency agile nonlinear absorption.

  DOI：

  10.1021/acs.inorgchem.5b01767

文献信息

• Naphtho[1,2-<i>c</i>:5,6-<i>c</i>′]bis[1,2,5]thiadiazole-Containing π-Conjugated Compound: Nonfullerene Electron Acceptor for Organic Photovoltaics
  作者：Shreyam Chatterjee、Yutaka Ie、Makoto Karakawa、Yoshio Aso

  DOI：10.1002/adfm.201504153

  日期：2016.2

  it is still challenging due to the insufficiency of both the variety of effective electron‐deficient units and certain guidelines for the design of such materials. This work focusses on naphtho[1,2‐c:5,6‐c′]bis[1,2,5]thiadiazole (NTz) as a key electron‐deficient unit. Therefore, a new electron‐accepting π‐conjugated compound (NTz‐Np), whose structure is based on the combination of NTz and the fluorene‐containing

  近年来，对于实现高功率转换效率（PCE），适用于有机光伏（OPV）的非富勒烯受体材料的开发引起了相当大的关注。但是，由于各种有效的电子不足单元的不足和此类材料设计的某些指导原则，它仍然具有挑战性。这项工作的重点是萘[1,2- c：5,6- c′] bis [1,2,5]噻二唑（NTz）作为关键的电子缺陷单元。因此，设计并合成了一种新的电子接受性π-共轭化合物（NTz-Np），其结构基于NTz和含芴的酰亚胺化末端单元（Np）的组合。NTz-Np化合物具有较窄的光能隙（1.73 eV），最低的未占据分子轨道的适当能级（−3.60 eV）和适度的电子迁移率（1.6×10 -5 cm 2 V -1 s -1），表明NTz-Np具有作为代表性供体聚（3-己基噻吩）（P3HT）的受体的适当特性。在与P3HT混合的基础上，基于NTz-Np的OPV器件具有较高的光伏性能，PCE为2.81％，在具有常规器件结构的P3HT
• Unexpectedly high second-order nonlinear optical properties of simple Ru and Pt alkynyl complexes as an analytical springboard for NLO-active polymer films
  作者：Alessia Colombo、Filippo Nisic、Claudia Dragonetti、Daniele Marinotto、Ivan Pietro Oliveri、Stefania Righetto、Maria Grazia Lobello、Filippo De Angelis

  DOI：10.1039/c4cc02432j

  日期：——

  The unexpectedly high quadratic hyperpolarizability values of simple Ru and Pt alkynyl complexes have been measured by the EFISH technique, and this prompted us to investigate their potential as molecular building blocks for composite films with second harmonic generation properties.

  简单的Ru和Pt炔基配合物的二次超极化率出乎意料地高，已通过EFISH技术进行了测量，这促使我们研究它们作为具有二次谐波生成特性的复合膜的分子构建基的潜力。
• Photophysics and Nonlinear Absorption of Gold(I) and Platinum(II) Donor–Acceptor–Donor Chromophores
  作者：Subhadip Goswami、Russell W. Winkel、Kirk S. Schanze

  DOI：10.1021/acs.inorgchem.5b01767

  日期：2015.10.19

  A series of Au(I) and Pt(II) acetylide complexes of a Itconjugated donor-acceptor-donor (D-A-D) chromophore were studied to develop quantitative structure property relationships for their photophysical and nonlinear optical properties. The D-A-D chromophore consists of a "TBT" unit, where T = 3-hexyl-2,5-thienylene and BTD = 2,1,3-benzothiadiazole, capped with ethynylene groups. The D-A-D chromophore is functionalized with Au(I)PR3 (R = -Me and -Ph) and trans-Pt(II)(PR3)(2)-CCPh (R = -Me and -Bu) auxochromes". All of the metal complexes were characterized by ground-state absorption, photoluminescence, nanosecond transient absorption, and two-photon absorption (2PA) spectroscopy. The experiments provided quantitative values of the photophysical parameters, including rates for radiative decay and intersystem crossing (ISC), triplet yields, and two-photon absorption cross sections. Pronounced solvatochromism in the fluorescence spectra suggests an enhanced dipole moment in the excited state of the complexes compared to the unmetalated TBT chromophore. The gold complexes feature larger fluorescence quantum yields and longer emission lifetimes compared to platinum. The Pt(II) complexes exhibit enhanced triplet triplet absorption, reduced triplet-state lifetimes, and larger singlet oxygen quantum yields, consistent with more efficient ISC compared to the Au(I) complexes. When excited by 100 fs pulses, all of the D-A-D chromophores exhibit moderate two-photon absorption in the near-infrared between 700 and 900 nm. The 2PA cross section for the Au(I) complexes is almost the same as the unmetalated D-A-D chromophore (similar to 100 GM). The Pt(II) complexes exhibit significantly enhanced 2PA compared to the other chromophores, reaching 1000 GM at 750 nm. Taken together, the results indicate that the Pt(II) center is considerably more effective in inducing singlet-triplet ISC and in enhancing the 2PA cross section. This result reveals the greater promise for Pt(II) acetylides in chromophores for temporal and frequency agile nonlinear absorption.