2,8,9a,9b-tetramethyl-5,6,9a,9b-tetrahydro-4H-indeno[5,4-b:6,7-b']dithiophen-4-one | 1448540-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2,8,9a,9b-tetramethyl-5,6,9a,9b-tetrahydro-4H-indeno[5,4-b:6,7-b']dithiophen-4-one
• CAS: 1448540-13-3
• 化学式: C₁₇H₁₈OS₂
• 分子量: 302.461
• InChiKey: KJTCVNHQRLLFIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,8,9a,9b-tetramethyl-5,6,9a,9b-tetrahydro-4H-indeno[5,4-b:6,7-b']dithiophen-4-one 生成 2,3-bis(2,5-dimethylthiophen-3-yl)cyclopent-2-en-1-one
  参考文献：
  名称：

  6,6a-二氢戊二烯-2（1 H）-一个乙烯“桥”的荧光光致变色二硫杂环丁烷的合成及光谱性质

  摘要：

  制备6,6a-二氢戊二烯-2（1 H）-one衍生物的另一种合成策略，包括区域选择性α阶段已经提出了环戊烯酮体系的溴化。该方法连同溴化过程包括将4-芳基-3-氧代丁酸乙酯与溴代环戊烯酮进行烷基化和烷基化产物的分子内碳环化反应。对环化反应进行了详细的研究，发现主产物和副产物的产率强烈依赖于碱浓度，该方法还可用于设计8,8a-dihydrocyclopenta [a] inden-2（1H） -一个单位。研究了所得化合物的光谱性质，发现五烯酮衍生物以及起始的环戊烯酮均表现出光致变色性质。另外，与后者不同，前者也是荧光的。

  DOI：

  10.1016/j.dyepig.2014.04.040
• 作为产物：
  描述：

  2,3-bis(2,5-dimethylthiophen-3-yl)cyclopent-2-en-1-one 生成 2,8,9a,9b-tetramethyl-5,6,9a,9b-tetrahydro-4H-indeno[5,4-b:6,7-b']dithiophen-4-one
  参考文献：
  名称：

  6,6a-二氢戊二烯-2（1 H）-一个乙烯“桥”的荧光光致变色二硫杂环丁烷的合成及光谱性质

  摘要：

  制备6,6a-二氢戊二烯-2（1 H）-one衍生物的另一种合成策略，包括区域选择性α阶段已经提出了环戊烯酮体系的溴化。该方法连同溴化过程包括将4-芳基-3-氧代丁酸乙酯与溴代环戊烯酮进行烷基化和烷基化产物的分子内碳环化反应。对环化反应进行了详细的研究，发现主产物和副产物的产率强烈依赖于碱浓度，该方法还可用于设计8,8a-dihydrocyclopenta [a] inden-2（1H） -一个单位。研究了所得化合物的光谱性质，发现五烯酮衍生物以及起始的环戊烯酮均表现出光致变色性质。另外，与后者不同，前者也是荧光的。

  DOI：

  10.1016/j.dyepig.2014.04.040

文献信息

• Photo- and PH-switchable fluorescent diarylethenes based on 2,3-diarylcyclopent-2-en-1-ones with dialkylamino groups
  作者：Valerii Z. Shirinian、Dmitry V. Lonshakov、Andrey G. Lvov、Alexey M. Kavun、Anton V. Yadykov、Mikhail M. Krayushkin

  DOI：10.1016/j.dyepig.2015.09.027

  日期：2016.1

  groups-comprising diarylethenes of 2,3-diarylcyclopent-2-en-1-one (DCP) series have been synthesized and its photochromic, fluorescent as well as acidochromic features have been investigated. It was shown that photochromic properties of the substances depend strong on their structures; the non-symmetry of the photochromic molecule is a powerful tool to properly control and tune the parameters of diarylethenes. It

  合成了新的含2,3-二芳基环戊-2-en-1-one（DCP）系列二烷氨基的二芳烃，并研究了其光致变色，荧光和酸性变色特征。结果表明，这些物质的光致变色特性强烈依赖于其结构。光致变色分子的非对称性是正确控制和调整二芳烃的参数的有力工具。已经发现合成的最有希望的DCP是在乙烯“桥”中而不是芳基部分中含有二烷基氨基的那些，因为它们具有光和pH可转换的发射以及热稳定性。已经确定，在苯戊烯酮环的第二位置引入苯残基导致光致变色性质的消失。
• New fluorescent switches based on photochromic 2,3-diarylcyclopent-2-en-1-ones and 6-ethoxy-3-methyl-1H-phenalen-1-one
  作者：Dmitry V. Lonshakov、Valerii Z. Shirinian、Andrey G. Lvov、Boris V. Nabatov、Mikhail M. Krayushkin

  DOI：10.1016/j.dyepig.2012.12.019

  日期：2013.5

  New fluorescent switches with 2,3-diarylcyclopent-2-en-1-ones as the photochromic component and 6-ethoxy-3-methyl-1H-phenalen-1-one as the fluorophore have been prepared. Two approaches to develop the photoswitches have been applied. The first involves covalent binding of the fluorophore to photochromic diarylethene molecule by ether linkage. The second type of fluorescent switch was been prepared

  制备了以2，3-二芳基环戊-2-烯-1-酮为光致变色组分和6-乙氧基-3-甲基-1 H-苯并-1-酮为荧光团的新型荧光开关。已经应用了两种开发光电开关的方法。首先涉及荧光团通过醚键与光致变色二芳基乙烯分子的共价结合。通过将光致变色的2，3-二芳基环戊-2-烯-1-酮和6-乙氧基-3-甲基-1 H-苯并-1-酮以各种比例混合来制备第二种类型的荧光开关。已经研究了荧光开关的光谱特性，并讨论了荧光猝灭的可能方法。
• New thermally stable photochromic di(het)arylethenes of the cyclopentenone series
  作者：D. V. Lonshakov、V. Z. Shirinian、A. G. Lvov、M. M. Krayushkin

  DOI：10.1007/s11172-012-0243-y

  日期：2012.9

  Oxidation of 2,3-diarylcyclopent-2-en-1-ones with m-chloroperoxybenzoic acid gave new thermally stable sulfone derivatives of photochromic diarylethenes. The spectral properties of the compounds obtained (the wavelengths of the maxima of the absorption bands of their initial and cyclic forms, the quantum yields of photocyclization and photobleaching reactions) as well as their thermal stability and fatigue resistance were examined. The relationship between the structures of the synthesized compounds and their photochromic properties was determined. The energy differences between the ground-state molecules of the starting and photoinduced isomers of 2,3-diarylcyclopent-2-en-1-ones were calculated by the DFT/B3LYP1 method with the 6-31G(d) basis set. The calculated energy differences can be used to predict and explain such spectral characteristics of photochromic diarylethenes as the thermal stability of photoinduced isomers and the quantum yields of cycloreversion reactions.

  用间氯过苯甲酸氧化 2,3-二芳基环戊-2-en-1-酮，得到光致变色二芳基乙烯的新型热稳定砜衍生物。检查了所得化合物的光谱特性（其初始形式和环状形式的吸收带最大值的波长、光环化和光漂白反应的量子产率）以及它们的热稳定性和抗疲劳性。确定了合成化合物的结构与其光致变色性能之间的关系。通过 DFT/B3LYP1 方法和 6-31G(d) 基组计算 2,3-二芳基环戊-2-en-1-酮的起始异构体和光诱导异构体的基态分子之间的能量差。计算出的能量差可用于预测和解释光致变色二芳基乙烯的光谱特性，例如光致异构体的热稳定性和环化回复反应的量子产率。
• Synthesis and spectral properties of photochromic cyclopentenone diarylethenes with an additional π system in the ethene bridge
  作者：Dmitry V. Lonshakov、Valerii Z. Shirinian、Andrey G. Lvov、Mikhail M. Krayushkin

  DOI：10.1016/j.mencom.2013.09.010

  日期：2013.9

  Photochromic diarylethenes with an additional p system in the ethene bridge were synthesized by the condensation of 2,3-bis(2,5-di- methyl-3-thienyl)cyclopent-2-en-1-one with aromatic aldehydes. Absorption bands maxima of the initial and cyclic forms of the substances were determined and their thermal stability was studied.

  通过2,3-双（2,5-二甲基-3-噻吩基）环戊-2-烯-1-酮与芳香族醛的缩合合成乙烯桥中带有p体系的光致变色二烯基蒽。确定了物质的初始和循环形式的最大吸收带，并研究了它们的热稳定性。
• Kinetics and mechanism of photochromic transformations of a 2,3-diarylcyclopentenone
  作者：V. V. Semionova、E. M. Glebov、A. B. Smolentsev、V. V. Korolev、V. P. Grivin、V. F. Plyusnin、V. Z. Shirinian

  DOI：10.1134/s0023158415030180

  日期：2015.5

  Photochemistry of recently synthesized 2,3-bis-(2,5-dimethylthiophen-3-yl-cyclopent-2-en-1-one) (diarylcyclopentenone, 1A) as a characteristic representative of photochromic 2,3-diarylcyclopent-2-en-1-ones (DCPs) was examined by means of stationary an nanosecond laser flash photolysis. Quantum yields of forward and backward photochemical reactions and molar absorption coefficient of the closed form were measured. Contradictions in the literature values of these parameters were eliminated. In laser flash photolysis experiments the formation of the 1A open form triplet state was exhibited, and the rate constants of the reactions of its decay were measured. 1A demonstrates rather low fatigue resistance, as any of other DCPs. In spite of the triplet state formation, photodegradation of 1A is not caused by the reactions of singlet oxygen.