(E)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide

• 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: (E)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide
• 英文别名: 2-thiophenecarboxaldehyde 2-thienylhydrazone；N'-(2-thienylmethylene)-2-thiophenecarbohydrazide；N-[(E)-thiophen-2-ylmethylideneamino]thiophene-2-carboxamide
• 化学式: C₁₀H₈N₂OS₂
• 分子量: 236.318
• InChiKey: BFQKAYQRWCAVAT-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide 以 乙腈 为溶剂， 反应 0.17h， 生成 (Z)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519
• 作为产物：
  描述：

  (Z)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide 以 乙腈 为溶剂， 反应 2.0h， 生成 (E)-N'-(thiophen-2-ylmethylene)thiophene-2-carbohydrazide
  参考文献：
  名称：

  Acylhydrazones as Widely Tunable Photoswitches

  摘要：

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.

  DOI：

  10.1021/jacs.5b09519

文献信息

• Co(II) Acetate‐Assisted Direct Synthesis of Acyl Hydrazones from Acyl Hydrazides under Mild Conditions
  作者：Adwitiya Pal、Krishna Mohan Das、Subham Sau、Arunabha Thakur

  DOI：10.1002/asia.202300755

  日期：2023.11.16

  efficient method to prepare multi-dynamic acyl (aryl and heteroaryl) hydrazones from acyl hydrazides has been achieved by using mild base K2CO3 and commercially available Co(OAc)2.4H2O salt as catalyst under mild reaction conditions with methanol as solvent. Additionally, the E/Z photoswitching behavior of some of the new acyl hydrazones has been witnessed by UV-vis spectroscopy.

  以弱碱K 2 CO 3和市售Co(OAc) 2 .4H 2 O盐为催化剂，在温和条件下，实现了一种原子经济且高效的由酰肼制备多动力酰基（芳基和杂芳基）腙的方法。反应条件以甲醇为溶剂。此外，一些新型酰基腙的E/Z光开关行为已被紫外-可见光谱证实。
• Synthesis and biological evaluation of arene ruthenium(II) complexes containing thiophene benzhydrazone derivative ligands
  作者：Charlestine Soh、Lathewdeipor Shadap、Mohan Rao Kollipara、Jaya Lakshmi Tyagi、Krishna Mohan Poluri、Yurij Mozharivskyj、E.K. Rymmai

  DOI：10.1016/j.jorganchem.2022.122559

  日期：2023.1

  synthesis of eight new ruthenium(II) thiophene benzhydrazone complexes (1–8) having the general formula [(η6-arene)Ru(L)Cl] (arene: benzene or p-cymene; L: bidentate substituted thiophenebenzhydrazone derivatives) has been described. They have been isolated as neutral mononuclear N∩O chelating ruthenium(II) complexes. When further reacted with sodium azide in methanol, these neutral ruthenium(II) thiophenebenzhydrazone

  一种具有通式 [( η 6 -arene)Ru(L)Cl]的八种新型钌 (II) 噻吩苯并腙配合物 ( 1–8)的便捷合成（芳烃：苯或对伞花烃；L：双齿取代的噻吩苯并腙衍生物) 进行了说明。它们已被分离为中性单核 N∩O 螯合钌 (II) 络合物。当在甲醇中进一步与叠氮化钠反应时，这些中性的钌 (II) 噻吩苯并腙络合物生成相应的叠氮基钌络合物 ( 9–16). 通过 IR、UV-Vis、NMR 和 ESI-MS 光谱方法对复合物进行了表征。使用单晶 X 射线衍射研究确定了代表性复合物的固态分子结构，复合物的几何形状为伪八面体，类似于钢琴凳结构。N∩O结合方式是通过偶氮甲碱氮和亚胺酸氧形成五元螯合环。所有复合物和配体都经过彻底筛选，用于抗菌和抗氧化活性研究，其中很少有复合物对革兰氏阳性细菌菌株（即金黄色葡萄球菌和苏云金芽孢杆菌）表现出抗菌活性。复合物7对金黄色葡萄球菌表现出最高的细菌抑制作用，而复合物7和8对B
• Acylhydrazones as Widely Tunable Photoswitches
  作者：Derk Jan van Dijken、Petr Kovaříček、Svante P. Ihrig、Stefan Hecht

  DOI：10.1021/jacs.5b09519

  日期：2015.12.2

  Molecular photoswitches have attracted much attention in biological and materials contexts. Despite the fact that existing classes of these highly interesting functional molecules have been heavily investigated and optimized, distinct obstacles and inherent limitations remain. Considerable synthetic efforts and complex structure property relationships render the development and exploitation of new photoswitch families difficult. Here, we focus our attention on acylhydrazones: a novel, yet underexploited class of photochromic molecules based on the imine structural motif. We optimized the synthesis of these potent photoswitches and prepared a library of over 40 compounds, bearing different substituents in all four crucial positions of the backbone fragment, and conducted a systematic study of their photochromic properties as a function of structural variation. This modular family of organic photoswitches offers a unique combination of properties and the compounds are easily prepared on large scales within hours, through an atom-economic synthesis, from commercially available starting materials. During our thorough spectroscopic investigations, we identified photoswitches covering a wide range of thermal half-lives of their (Z)-isomers, from short-lived T-type to thermally stable P-type derivatives. By proper substitution, excellent band separation between the absorbance maxima of (E)- and (Z)-isomers in the UV or visible region could be achieved. Our library furthermore includes notable examples of rare negative photochromic systems, and we show that acylhydrazones are highly fatigue resistant and exhibit good quantum yields.