4-(4-hydroxy-3-propylphenylazo)pyridine | 312693-99-5

• 分子结构分类: 有机化合物
• 英文名称: 4-(4-hydroxy-3-propylphenylazo)pyridine
• CAS: 312693-99-5
• 化学式: C₁₄H₁₅N₃O
• 分子量: 241.293
• InChiKey: BBXGFZXXADBYAD-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  57.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-hydroxy-3-propylphenylazo)pyridine 在 氢氧化钾 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 11-[2-Propyl-4-(pyridin-4-ylazo)-phenoxy]-undecanoic acid
  参考文献：
  名称：

  Self-Assembly of Amphoteric Azopyridine Carboxylic Acids:  Organized Structures and Macroscopic Organized Morphology Influenced by Heat, pH Change, and Light

  摘要：

  In this paper, we describe the synthesis of novel amphoteric azopyridine carboxylic acids (2b, 3a, 3b, 4a, and 4b), having both a carboxyl group as a hydrogen donor and a pyridyl group as an acceptor at each molecular terminus, and their self-organization, which is markedly affected by external stimuli including heat, pH changes, and light. The amphoteric compounds form intermolecular hydrogen bonds between pyridyl and carboxyl groups in a head-to-tail manner in the solid state to give linear pseudopolymer structures, as supported by FT-IR analysis. Heating and cooling across their melting points induced thermoreversible supramolecular depolymerization to and polymerization from small molecular components of monomers and the corresponding carboxylic acid dimers. In alkaline aqueous media, these amphoteric compounds, dissolved as carboxylate anions, were gradually neutralized by atmospheric carbon dioxide, leading to their deposition as novel fibrous materials from 3b and 4b, substituted with a propyl group at the phenyl ring, and as leaflet crystals from 3a and 4a bearing no substituent. FT-IR and X-ray diffraction measurements supported the conclusion that the formation of fibrous materials from 3b and 4b arises from their intermolecular hydrogen bonding in a head-to-tail manner as well as the suppressive effect of propyl substitution on the pi-pi stacking of the molecules. UV irradiation of alkaline solutions of 4b resulted in the modification of the morphology of fibrous materials, probably because the photoisomerized Z-isomer of 4b affected the nucleation process in the fibrous formation. These results suggest that morphological properties of these macroscopic self-assemblages are tunable by appropriate choices of environmental stimuli such as heat, pH, and light.

  DOI：

  10.1021/ja001790f
• 作为产物：
  描述：

  4-氨基吡啶 、 2-正丙基苯酚 在 盐酸 、 sodium hydroxide 、 sodium nitrate 作用下， 以30%的产率得到4-(4-hydroxy-3-propylphenylazo)pyridine
  参考文献：
  名称：

  Self-Assembly of Amphoteric Azopyridine Carboxylic Acids:  Organized Structures and Macroscopic Organized Morphology Influenced by Heat, pH Change, and Light

  摘要：

  In this paper, we describe the synthesis of novel amphoteric azopyridine carboxylic acids (2b, 3a, 3b, 4a, and 4b), having both a carboxyl group as a hydrogen donor and a pyridyl group as an acceptor at each molecular terminus, and their self-organization, which is markedly affected by external stimuli including heat, pH changes, and light. The amphoteric compounds form intermolecular hydrogen bonds between pyridyl and carboxyl groups in a head-to-tail manner in the solid state to give linear pseudopolymer structures, as supported by FT-IR analysis. Heating and cooling across their melting points induced thermoreversible supramolecular depolymerization to and polymerization from small molecular components of monomers and the corresponding carboxylic acid dimers. In alkaline aqueous media, these amphoteric compounds, dissolved as carboxylate anions, were gradually neutralized by atmospheric carbon dioxide, leading to their deposition as novel fibrous materials from 3b and 4b, substituted with a propyl group at the phenyl ring, and as leaflet crystals from 3a and 4a bearing no substituent. FT-IR and X-ray diffraction measurements supported the conclusion that the formation of fibrous materials from 3b and 4b arises from their intermolecular hydrogen bonding in a head-to-tail manner as well as the suppressive effect of propyl substitution on the pi-pi stacking of the molecules. UV irradiation of alkaline solutions of 4b resulted in the modification of the morphology of fibrous materials, probably because the photoisomerized Z-isomer of 4b affected the nucleation process in the fibrous formation. These results suggest that morphological properties of these macroscopic self-assemblages are tunable by appropriate choices of environmental stimuli such as heat, pH, and light.

  DOI：

  10.1021/ja001790f

文献信息

• STYRENE POLYMER AND MANUFACTURING METHOD THEREFOR
  申请人：Nippon Soda Co., Ltd.

  公开号：EP2511309A1

  公开（公告）日：2012-10-17

  There is provided a method for manufacturing a styrene polymer having a low number average molecular weight and a low polydispersity index, wherein the polymer has a number average molecular weight of 2000 or less and a polydispersity index of 1.01 to 1.10. For this purpose, the method includes polymerizing a styrene monomer in a solvent comprising an ether group-containing solvent in the presence of a polymerization initiator represented by formula [II] (wherein R1 represents a hydrogen atom, an alkyl group, or a phenyl group; R2 represents an alkyl group; R3 represents an alkyl group or an alkoxy group, wherein when n is 2 or more, R3 is the same or different from each other; and n represents an integer of 0 to 5), an organometallic compound represented by formula [III]: (R8)mM [III] (wherein R8 represents an alkyl group or an aryl group, wherein when m is 2 or more, R8 is the same or different from each other; M represents an atom belonging to Group 2, 12 or 13 of the long period type periodic table; and m represents the valence of M), and an organic potassium compound, at a temperature between -10°C or higher and a boiling point of the solvent or lower.

  本发明提供了一种制造具有低平均分子量和低多分散指数的苯乙烯聚合物的方法，其中该聚合物的平均分子量为 2000 或更低，多分散指数为 1.01 至 1.10。为此目的，该方法包括在由含醚基的溶剂组成的溶剂中，在式[II]代表的聚合引发剂（其中R1代表氢原子、烷基或苯基；R2代表烷基；R3代表烷基或烷氧基，其中当n为2或2以上时，R3彼此相同或不同；n代表0至5的整数）、式[III]代表的有机金属化合物的存在下，聚合苯乙烯单体：(R8)mM[III]（其中 R8 代表烷基或芳基，当 m 为 2 或更多时，R8 彼此相同或不同；M 代表属于长周期类型元素周期表中第 2、12 或 13 族的原子；m 代表 M 的化合价），以及有机钾化合物，温度在-10℃或更高和溶剂沸点或更低之间。