5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile | 51802-55-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile
• 英文别名: 2,3-dicyano-5,7-dimethyl-6H-1,4-diazepine；2,3-dicyano-5,7-dimethyl[1,4]diazepine；5,7-dimethyl-6H-[1,4]diazepine-2,3-dicarbonitrile
• CAS: 51802-55-2
• 化学式: C₉H₈N₄
• mdl: MFCD03618030
• 分子量: 172.189
• InChiKey: MAFHEXKPIODQPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  72.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile 在 sodium hydroxide 、 碘苯二乙酸 、 双氧水 作用下， 以 甲醇 、 苯 为溶剂， 反应 67.0h， 生成 3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo<4.2.1>nona-2,4-diene
  参考文献：
  名称：

  Ramakrishnan, V. T.; Boyer, Joseph H., Heterocycles, 1981, vol. 16, # 8, p. 1345 - 1351

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-dicyano-1,6-dimethyl-2,5-diaza-7,8-dioxabicyclo<4.2.1>non-3-ene 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 17.0h， 以72%的产率得到5,7-dimethyl-6H-1,4-diazepine-2,3-dicarbonitrile
  参考文献：
  名称：

  Ramakrishnan, V. T.; Boyer, Joseph H., Heterocycles, 1981, vol. 16, # 8, p. 1345 - 1351

  摘要：

  DOI：

文献信息

• Optical Properties of Novel 2,3-Dicyano-5-methyl-6<i>H</i>-1,4-diazepine Dyes in the Solid State
  作者：Emi Horiguchi、Shinya Matsumoto、Kazumasa Funabiki、Masaki Matsui

  DOI：10.1246/bcsj.78.1167

  日期：2005.6

  Novel nonplanar fluorescent dyes, 2,3-dicyano-7-methyl-6H-1,4-diazepines, were synthesized. The fluorescence intensity of 6-substituted 2,3-dicyano-5-[4-(diethylamino)styryl]-7-methyl-6H-1,4-diazepines in vapor-deposited film was on the order of the substituent at the 6-position: n-Bu, Et > t-Bu, H. That of 2,3-dicyano-5-[4-(dialkylamino)styryl]-6-ethyl-7-methyl-6H-1,4-diazepines in the solid state was on the order of the alkyl group: CH2(3,5-(di-t-Bu)C6H3) > Bn > Et. Thus, the fluorescence intensity in the solid state basically increased with the bulkiness of the substituents on the chromophoric system. X-ray structure analysis clearly showed that the substituent at the 6-position and the dialkylamino moiety should inhibit intermolecular interactions between the chromophores so as to enhance the fluorescence intensity in the solid state.

  合成了新型非平面荧光染料，2,3-二氰基-7-甲基-6H-1,4-二氮杂萘。6-取代的2,3-二氰基-5-[4-(二乙氨基)苯乙烯]-7-甲基-6H-1,4-二氮杂萘在蒸汽沉积薄膜中的荧光强度受6位取代基的影响顺序为：n-丁基、乙基 > t-丁基、氢。2,3-二氰基-5-[4-(二烷基氨基)苯乙烯]-6-乙基-7-甲基-6H-1,4-二氮杂萘在固态下的荧光强度受烷基基团影响的顺序为：CH2(3,5-(二-t-丁基)C6H3) > 苄基 > 乙基。因此，固态下的荧光强度基本上随着染料色素体系中取代基的体积增大而增加。X射线结构分析清楚地表明，6位的取代基和二烷基氨基部分应抑制染料色素之间的分子间相互作用，从而增强固态下的荧光强度。
• Synthesis of Near-Infrared Fluorescent 2,3-Dicyano-6<i>H</i>-1,4-diazepines
  作者：Emi Horiguchi、Kazumasa Funabiki、Masaki Matsui

  DOI：10.1246/bcsj.78.316

  日期：2005.2

  A series of novel 5-(2-arylethenyl)-, 5-(4-arylbutadienyl)-, 5-(6-arylhexatrienyl)-, and 5-(8-octatetraenyl)-, 5-aryl-7-(2-arylethenyl)-, and 5,7-bis(2-arylethenyl)-2,3-dicyano-6H-1,4-diazepines were synthesized by the reactions of 2,3-dicyano-5-methyl-6H-1,4-diazepines with aromatic aldehydes. These compounds showed intramolecular charge-transfer chromophoric systems from the arylethenyl to the 2,3-dicyano-6H-diazepine moieties. The shifts in UV–vis absorption bands were estimated by calculating the HOMO and LUMO energy levels. 2-(9-Julolidyl)ethenyl derivative showed the most intense fluorescence. The 6-(9-julolidyl)-1,3,5-hexatrienyl and 8-(9-julolidyl)-1,3,5,7-octatetraenyl derivatives exhibited the fluorescence maxima (Fmax) at 780 and 842 nm, respectively.

  一系列新型 5-(2-芳基乙烯基)-、5-(4-芳基丁二烯基)-、5-(6-芳基己三烯基)-和 5-(8-辛四烯基)-、5-芳基-7-(2-芳基乙烯基)-和 5、通过 2,3-二氰基-5-甲基-6H-1,4-二氮杂卓与芳香醛的反应，合成了 7-双（2-芳基乙烯基）-2,3-二氰基-6H-1,4-二氮杂卓。这些化合物显示了从芳基乙烯基到 2,3-二氰基-6H-二氮杂卓的分子内电荷转移色素系统。通过计算 HOMO 和 LUMO 能级，估算了紫外-可见吸收带的移动。2-(9-julolidyl)ethenyl 衍生物显示出最强烈的荧光。6-(9-julolidyl)-1,3,5-hexatrienyl 和 8-(9-julolidyl)-1,3,5,7-octatetraenyl 衍生物的荧光最大值（Fmax）分别为 780 纳米和 842 纳米。
• Nitrogen-containing heterocyclic compound
  申请人：——

  公开号：US20030057826A1

  公开（公告）日：2003-03-27

  A nitrogen-containing heterocyclic compound represented by the following formula (I): 1 wherein X 1 and X 2 each represent an electron attractive group such as a cyano group; and the rings Z 1 and Z 2 each represent a hydrocarbon ring or a heterocycle (e.g., benzene ring having an electron donative group such as hydroxyl group, an alkoxy group, amino group and an N-substituted amino group, or a condensed ring being a benzene ring condensed with a heterocycle having a nitrogen atom as a hetero atom) is provided. An organic EL device is obtained by allowing an organic layer containing the compound described-above to be interposed between a pair of electrodes. The present invention provides a nitrogen-containing heterocyclic compound useful as a functional material and a process for producing the same, and an organic EL device using the same.

  提供一种含氮杂环化合物，其化学式如下（I）：其中X1和X2各代表一个电子吸引基团，如氰基；环Z1和Z2各代表一个碳氢环或杂环（例如，苯环具有一个电子给体基团，如羟基、烷氧基、氨基和N-取代氨基，或者是一个与氮原子作为杂原子的杂环缩合环的苯环）。通过在一对电极之间插入含有上述化合物的有机层，可以获得有机EL器件。本发明提供了一种作为功能材料有用的含氮杂环化合物，以及制备该化合物的方法和使用该化合物的有机EL器件。
• Azepine compounds
  申请人：——

  公开号：US20020091256A1

  公开（公告）日：2002-07-11

  The azepine compound capable of emitting a light by light-irradiation or action of an electric field is represented by the following formula (I) or (II): 1 wherein X 1 and X 2 are the same or different, each representing an electron attractive group; R 1 represents a hydrogen atom, an alkyl group, an aryl group, an aralkyl group, or an alkoxy group; R 2 represents an amino group or an N-substituted amino group, or, in the formula (I), R 2 bonds a carbon atom adjacent to a ring Z to form a ring; and the ring Z represents a hydrocarbon ring which may have a substituent or a heterocycle which may have a substituent. The compound is useful as a functional material, thus, an organic electroluminescence device can be obtained by interposing an organic layer composed of the above compound between a pair of electrodes.

  具有通过光照射或电场作用而发出光的氮杂环化合物的化学式如下（I）或（II）：1其中，X1和X2相同或不同，分别表示电子吸引基团；R1表示氢原子、烷基、芳基、芳基烷基或烷氧基；R2表示氨基或N-取代氨基，或在式（I）中，R2与环Z相邻的碳原子连接以形成环；环Z表示可能具有取代基的碳氢环或可能具有取代基的杂环。该化合物可用作功能材料，因此，在一对电极之间插入由上述化合物组成的有机层可获得有机电致发光器件。
• Synthesis, characterization and photophysical properties of novel 5,7-disubstituted-1,4-diazepine-2,3-dicarbonitriles
  作者：Ewelina Wieczorek、Mateusz Gierszewski、Lukasz Popenda、Ewa Tykarska、Maria Gdaniec、Stefan Jurga、Marek Sikorski、Jadwiga Mielcarek、Jaroslaw Piskorz、Tomasz Goslinski

  DOI：10.1016/j.molstruc.2016.01.032

  日期：2016.4

  was observed. Experimental data for diazepine derivative containing 2-(4- tert -butylphenyl)ethenyl substituents were verified by X-ray crystallography. The obtained compounds were subjected to photophysical studies. In the UV–Vis absorption spectra two characteristic bands were found. In the solvatochromic study, the first band maxima were located in the range of 384–418 nm, whereas second band maxima

  摘要 三种 5,7-二取代-1,4-二氮杂-2,3-二腈与庞大的 2-(3,5-二溴苯基)乙烯基、2-(4-叔丁基苯基)乙烯基和 2-(3,5-合成二苄氧基苯基）乙烯基取代基，并使用 UV-Vis、MS ES、元素分析和 NMR 光谱对其进行表征。NMR数据表明所有获得的化合物的二氮杂环均采用6 H-互变异构形式。此外，观察到苯乙烯基取代基内的反式异构现象。含有 2-(4-叔丁基苯基) 乙烯基取代基的二氮杂衍生物的实验数据通过 X 射线晶体学验证。对所得化合物进行光物理研究。在紫外-可见吸收光谱中发现了两个特征带。在溶剂致变色研究中，第一条带最大值位于 384-418 nm 范围内，而第二波段最大值在 313-345 nm 范围内。新型二氮杂衍生物的荧光强度在所有溶剂中都相当低，2-(3,5-二溴苯基)乙烯基的荧光量子产率Ф F = 10 -4 ，2-(4-叔-)的荧光量子产率Ф F = 10