2,2''-dimethyl-2',5'-dihydro[3,3':4',3''-terthiophene]-5,5''-dicarbaldehyde | 528604-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,2''-dimethyl-2',5'-dihydro[3,3':4',3''-terthiophene]-5,5''-dicarbaldehyde
• 英文别名: 3,4-bis-(5-formyl-2-methylthien-3-yl)-2,5-dihydrothiophene；3,4-bis(5-formyl-2-methylthien-3-yl)-2,5-dihydrothiophene；4-[4-(5-Formyl-2-methylthiophen-3-yl)-2,5-dihydrothiophen-3-yl]-5-methylthiophene-2-carbaldehyde
• CAS: 528604-90-2
• 化学式: C₁₆H₁₄O₂S₃
• 分子量: 334.484
• InChiKey: HWPNXONYOAOCRV-UHFFFAOYSA-N

物化性质

• 沸点：
  557.2±50.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2''-dimethyl-2',5'-dihydro[3,3':4',3''-terthiophene]-5,5''-dicarbaldehyde 在 C₃₈H₂₆N₃OPt⁽¹⁺⁾*ClO₄^(1-) 作用下， 以 乙腈 为溶剂， 以80%的产率得到2,2''-dimethyl[3,3':4',3''-terthiophene]-5,5''-dicarbaldehyde
  参考文献：
  名称：

  Visible Light-Induced Synthesis of 3,4-Diarylthiophenes from 3,4-Diaryl-2,5-dihydrothiophenes

  摘要：

  Using a catalytic amount of platinum(II) terpyridyl complex 3, 3,4-diarylthiophenes (2a-f) could be synthesized from 3,4-diaryl-2,5-dihydrothiophenes (1a-f) under visible light (lambda > 450 nm) irradiation in degassed CH3CN. Spectroscopic study and product analysis reveal that the reaction is initiated by photoinduced electron transfer from 3,4-diaryl-2,5-dihydrothiophenes to platinum (II) complex 3, leading to the formation of 3,4-diarylthiophenes.

  DOI：

  10.1021/jo3006123
• 作为产物：
  描述：

  2-氯-5-甲基噻吩 在 sodium sulfide 、 正丁基锂 、 三氯化铝 、 溴 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 74.75h， 生成 2,2''-dimethyl-2',5'-dihydro[3,3':4',3''-terthiophene]-5,5''-dicarbaldehyde
  参考文献：
  名称：

  具有2,5-二氢噻吩桥联单元的功能性二芳基乙烯的合成和光致变色性能。

  摘要：

  描述了一种具有2,5-二氢噻吩桥连单元的对称和非对称二噻吩乙烯衍生物的新颖合成途径。制备了一类新的功能性光致变色化合物，其显示出与已知的二芳烃类似的光致变色性质。[反应：看文字]

  DOI：

  10.1021/ol034166r

文献信息

• Selective photochromism and solvatochromism of a diarylethene with different bridge units
  作者：Huan-huan Liu、Yi Chen

  DOI：10.1039/c0jm02691c

  日期：——

  A photochromic diarylethene (1a) with three bis(thien-3-yl) systems, containing a 2,5-dihydrothiophene unit and two imidazole units, has been prepared. 1a shows selective photochromism: upon irradiation with 365 nm, one bis(thien-3-yl) system containing a 2,5-dihydrothiophene unit is selected to undergo photocyclization reaction to form ring-closed isomer 1b, the other two bis(thien-3-yl) systems containing imidazole units are photo-inactive. With 254 nm light irradiation, all three bis(thien-3-yl) systems undergo photocyclization reaction to produce ring-closed isomer 1c. Selective solvatochromism was also observed at a ring-closed state: only 1c showed solvatochromism, and the solvatochromism was dependent on the solvent donor numbers: with the increase of donor numbers of solvent, the absorption of 1c shifted to shorter wavelength.

  一种具有三个双(噻吩-3-基)系统的光变色日记酮 (1a) 被制备出来，包含一个 2,5-二氢噻吩单元和两个咪唑单元。1a 显示出选择性光变色性：在365 nm照射下，其中一个包含2,5-二氢噻吩单元的双(噻吩-3-基)系统被选择进行光环化反应，形成环闭异构体 1b，而另外两个包含咪唑单元的双(噻吩-3-基)系统则不活跃。在254 nm光照射下，所有三个双(噻吩-3-基)系统都发生光环化反应，产生环闭异构体 1c。在环闭状态下还观察到了选择性溶剂变色性：只有 1c 显示出溶剂变色性，且该变色性依赖于溶剂的供体数量：随着溶剂供体数量的增加，1c 的吸收向更短波长偏移。
• Study on Photochromic Diarylethene with Phenolic Schiff Base:  Preparation and Photochromism of Diarylethene with Benzoxazole
  作者：Yi Chen、De X. Zeng

  DOI：10.1021/jo049565u

  日期：2004.7.1

  in the solution. In addition, a general preparation of 2-arylbenzoxazole from phenolic Schiff base in the conditions of base and phototrigger is demonstrated by employing phenolic Schiff bases with different substituted groups as template, and other conditions (solvents, in the presence and absence of oxygen) for preparation of benzoxazole from phenolic Schiff base are explored as well.

  具有酚席夫碱1a的光致变色二芳基乙烯可以在碱和光触发条件下容易地转化为具有苯并恶唑3a的光致变色二芳基乙烯。研究了它们的光致变色性质。他们表明，在光平稳平衡下，开环形式向闭环形式的转化约为。3a和1a分别为20％和10％，两种化合物的反向转化率几乎都是定量的。他们还表明，光平稳平衡的响应时间约为。3a和1a为0.5和5分钟分别在解决方案中。另外，通过在碱和光触发条件下，由酚基席夫碱制备2-芳基苯并恶唑的一般方法是通过使用具有不同取代基的酚基席夫碱作为模板，以及在其他条件下（溶剂，在有氧和无氧条件下）进行制备的。还探讨了从酚类席夫碱制备苯并恶唑的方法。
• Modulation of color change and photocyclization of diarylethene with metal complex
  作者：Huan-Huan Liu、Yi Chen

  DOI：10.1002/poc.1798

  日期：2011.6

  Modulation of color change and photocyclization of diarylethene with metal complex is described. A diarylethene derivative with 4‐(ethylideneamino) phenol group 1a is prepared and photochromic behavior is investigated. It is found that 1a exhibits ring‐opening and ring‐closing photoisomerization with UV/Vis light irradiation in solution. Addition of Cu(OAc)2 to the solution of 1a produces a metal complex

  描述了金属配合物对二芳基乙烯的颜色变化和光环化的调节。制备了具有4-（亚乙基氨基）苯酚基团1a的二芳基乙烯衍生物，并研究了光致变色行为。发现1a在溶液中具有UV / Vis光照射时会显示开环和闭环光异构化。在1a溶液中添加Cu（OAc）2会生成1a–Cu金属配合物，不仅会产生明显的颜色变化，而且还会显着促进光环化反应。版权所有©2010 John Wiley＆Sons，Ltd.
• Construction and properties of multi-addressable switching system based on a photochromic diarylethene
  作者：Huan-Huan Liu、Yi Chen

  DOI：10.1039/b812843j

  日期：——

  A multi-addressable switching system has been constructed by employing photochromic diarylethene 1a, which is obtained by coupling photochromic 3,4-bis(5-formyl-2-methylthien-3-yl)-2,5-dihydrothiophene with 8-hydroxy-2-methylquinoline, as model compound. It is found that 1a exhibits ring-opening and ring-closing photoisomerization with UV/Vis light irradiation. Addition of trifluoroacetic acid to solution of 1a produces protonated diarylethene 2a, and 2a also performs photochromic behavior with distinguished color change. Both protonated ring-open isomer 2a and ring-closed isomer 2b reverse back to 1a and 1b by neutralization with base solution. Besides, a complex diarylethene 3a is formed when boron trifluoride diethyl etherate is added to a solution of 1a, and it is found that 3a also undergoes excellent photoisomerization.

  以光致变色的 3,4-双（5-醛基-2-甲基噻吩-3-基）-2,5-二氢噻吩与 8-羟基-2-甲基喹啉偶联得到的光致变色二芳基噻吩 1a 为模型化合物，构建了一个多地址切换系统。研究发现，1a 在紫外/可见光照射下会出现开环和闭环光异构化现象。在 1a 的溶液中加入三氟乙酸会生成质子化的二芳基噻吩 2a，并且 2a 还具有光致变色行为，颜色变化明显。质子化的开环异构体 2a 和闭环异构体 2b 在用碱溶液中和后都会反转为 1a 和 1b。此外，在 1a 的溶液中加入三氟化硼二乙基醚酸盐后，会形成复杂的二元蒽 3a，而且发现 3a 也会发生极好的光异构化。
• Modulation of a fluorescent switch based on a controllable photochromic diarylethene shutter
  作者：Yi Chen、Nan Xie

  DOI：10.1039/b506381g

  日期：——

  A convenient system of modulation of a fluorescent switch based on photoisomerization of diarylethene has been demonstrated by employing 9,10-anthracenedinaphthalene 1 and benzothiazole diarylethene 2a as the fluorescence dye and the photochromic compound, respectively. The fluorescence change of 1 is modulated easily by photoisomerization of 2a, which is doped into the fluorescence dye, in solution as well as in a polymer film. The changes of fluorescence intensity of 1 between the “on” and “off” states are significant in both solution and polymer film and more than 20 cycles in solution and 10 cycles in polymer of fluorescence switching are achieved without distinguished change in fluorescence intensity.

  通过使用 9,10-蒽二萘 1 和苯并噻唑二连蒽 2a 分别作为荧光染料和光致变色化合物，证明了一种基于二连蒽光异构化的荧光开关调制便捷系统。掺入荧光染料的 2a 在溶液和聚合物薄膜中发生光异构化，很容易调节 1 的荧光变化。在溶液和聚合物薄膜中，1 在 "开启 "和 "关闭 "状态之间的荧光强度变化都很显著，在溶液中可实现 20 多个周期的荧光切换，在聚合物中可实现 10 个周期的荧光切换，而荧光强度不会发生明显变化。