4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline | 1301247-06-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline
• 英文别名: HTTQ；4,9-Bis(4-hexylthiophen-2-yl)-6,7-dithiophen-2-yl-[1,2,5]thiadiazolo[3,4-g]quinoxaline；4,9-bis(4-hexylthiophen-2-yl)-6,7-dithiophen-2-yl-[1,2,5]thiadiazolo[3,4-g]quinoxaline
• CAS: 1301247-06-2
• 化学式: C₃₆H₃₆N₄S₅
• 分子量: 685.039
• InChiKey: BWNJZFYVCIWWBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  193
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4,7-二溴-5,6-二硝基苯并[c][1,2,5]噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 铁粉 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 26.0h， 生成 4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline
  参考文献：
  名称：

  Synthesis of new donor–acceptor polymers containing thiadiazoloquinoxaline and pyrazinoquinoxaline moieties: low-band gap, high optical contrast, and almost black colored materials

  摘要：

  Two low band gap conjugated polymers, poly[4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline] (PHTTQ) and poly[5,10-bis(4-hexylthien-2-yl)-2,3,7,8-tetra(thien-2-yl)pyrazino[2,3-g]quinoxaline] (PHTPQ), consisting of alternating electron-rich 3-hexylthiophene and electron-deficient 6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TTQ) and 2,3,7,8-tetra(thien-2-yl)-2,3-dihydropyrazino[2,3-g]quinoxaline (TPQ) units were synthesized electrochemically. The structures of the pi-conjugated monomers were tailored using thiophene as the pendant group on the acceptor units (TTQ and TPQ). The electrochemical and optical properties of the polymers were investigated by cyclic voltammetry and UV-vis-NIR spectroscopy. The absorption spectra of PHTPQ revealing a 1.0 eV band gap, exhibited three maxima at 352 nm, 535 nm, and 750 nm. Consequently, its absorption spectra cover the region between 400 and 800 nm, which make the polymer almost black in appearance. PHTTQ shows lambda(max) value of 820 nm and a band gap of 0.8 eV which is very low among other [1,2,5]thiadiazolo[3,4-g]quinoxaline-containing donor-acceptor type polymers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.078

文献信息

• [EN] PHOTOACTIVE MATERIAL<br/>[FR] MATÉRIAU PHOTOACTIF
  申请人：[en]SUMITOMO CHEMICAL CO., LTD

  公开号：WO2021156605A1

  公开（公告）日：2021-08-12

  A material comprising an electron-accepting unit of formula (I): wherein Ar1 and Ar2 independently is a 5- or 6-membered aromatic or heteroaromatic ring or is absent; and each X is independently H or a substituent with the proviso that at least one X is an electron-withdrawing group and wherein X groups bound to adjacent carbon atoms may be linked to form an electron-withdrawing group. The material further comprises an electron-donating unit D comprising a fused or unfused furan or thiophene. The material may be a polymer comprising repeat units of formula (I). The material may be a non- polymeric compound. An organic photodetector may contain a bulk heterojunction layer containing an electron acceptor or an electron donor wherein at least one of the electron acceptor and electron donor contains a unit of formula (I).
• Synthesis of new donor–acceptor polymers containing thiadiazoloquinoxaline and pyrazinoquinoxaline moieties: low-band gap, high optical contrast, and almost black colored materials
  作者：Elif Kose Unver、Simge Tarkuc、Derya Baran、Cihangir Tanyeli、Levent Toppare

  DOI：10.1016/j.tetlet.2011.03.078

  日期：2011.5

  Two low band gap conjugated polymers, poly[4,9-bis(4-hexylthien-2-yl)-6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline] (PHTTQ) and poly[5,10-bis(4-hexylthien-2-yl)-2,3,7,8-tetra(thien-2-yl)pyrazino[2,3-g]quinoxaline] (PHTPQ), consisting of alternating electron-rich 3-hexylthiophene and electron-deficient 6,7-di(thien-2-yl)-[1,2,5]thiadiazolo[3,4-g]quinoxaline (TTQ) and 2,3,7,8-tetra(thien-2-yl)-2,3-dihydropyrazino[2,3-g]quinoxaline (TPQ) units were synthesized electrochemically. The structures of the pi-conjugated monomers were tailored using thiophene as the pendant group on the acceptor units (TTQ and TPQ). The electrochemical and optical properties of the polymers were investigated by cyclic voltammetry and UV-vis-NIR spectroscopy. The absorption spectra of PHTPQ revealing a 1.0 eV band gap, exhibited three maxima at 352 nm, 535 nm, and 750 nm. Consequently, its absorption spectra cover the region between 400 and 800 nm, which make the polymer almost black in appearance. PHTTQ shows lambda(max) value of 820 nm and a band gap of 0.8 eV which is very low among other [1,2,5]thiadiazolo[3,4-g]quinoxaline-containing donor-acceptor type polymers. (C) 2011 Elsevier Ltd. All rights reserved.