6-(4-ethynylbenzyl)-1,3,5-triazine-2,4-diamine | 1254568-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 6-(4-ethynylbenzyl)-1,3,5-triazine-2,4-diamine
• 英文别名: 6-[(4-Ethynylphenyl)methyl]-1,3,5-triazine-2,4-diamine；6-[(4-ethynylphenyl)methyl]-1,3,5-triazine-2,4-diamine
• CAS: 1254568-80-3
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: SOLWICWVHYQOBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  90.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(4-ethynylbenzyl)-1,3,5-triazine-2,4-diamine 、 N,N'-bis(3-azidopropyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-bis(dicarboximide) 在 copper(l) iodide 、 N,N-二异丙基乙胺 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 异丙醇 、 甲苯 为溶剂， 反应 7.0h， 以55%的产率得到5,6,12,13-tetrachloro-2,9-bis(3-(4-(4-((4,6-diamino-1,3,5-triazin-2-yl)methyl)phenyl)-1H-1,2,3-triazol-1-yl)propyl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone
  参考文献：
  名称：

  Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties

  摘要：

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.10.096
• 作为产物：
  描述：

  二聚氰胺 、 4-乙炔基苯乙腈 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以92.5%的产率得到6-(4-ethynylbenzyl)-1,3,5-triazine-2,4-diamine
  参考文献：
  名称：

  通过动态流变学的超分子聚合物的聚集和链动力学：团簇形成和自聚集。

  摘要：

  制备了带有氢键合单元的单官能和双官能链端的超分子聚异丁烯（PIB），并通过动态流变学研究了它们在熔融态下的缔合行为，并将其与溶液中的聚集进行了比较，旨在确定固态下的缔合动力学。将活性阳离子聚合与叠氮化物/炔烃“点击”反应或亲核取代反应结合在一起的制备方法，可以将完整的端基转化为最终的PIB聚合物，并用胸腺嘧啶或2,6-二氨基三嗪端基进行修饰，这已通过NMR和MALDI方法证明分子量约为3500至10000 g / mol。通过溶液共混制备这些具有特异性相互作用的胸腺嘧啶/三嗪部分的聚合物的化学计量混合物，并通过流变学测量研究温度依赖性动力学。在20-60°C的温度下，所有样品均显示出具有片状或部分交联结构的强热可逆聚集性，在〜80°C的温度下会发生聚集。由带有胸腺嘧啶和2，6-二氨基三嗪部分的各自双功能PIB形成具有桥联胶束结构的更复杂的聚集体。因此，除了特定的线性聚集体外，还必须考虑形成

  DOI：

  10.1021/ma101962y

文献信息

• Poly(ε-caprolactone)-poly(isobutylene): A crystallizing, hydrogen-bonded pseudo-block copolymer
  作者：Elena Ostas、Klaus Schröter、Mario Beiner、Tingzi Yan、Thomas Thurn-Albrecht、Wolfgang H. Binder

  DOI：10.1002/pola.24777

  日期：2011.8.1

  AbstractThe crystallization of block copolymers (BCPs) under homogeneous and heterogeneous nucleation is currently well understood revealing the strong interplay of crystallization in competition to microphase separation. This article reports investigations on synthesis and crystallization processes in weakly interacting supramolecular pseudo‐BCPs, composed of poly(ε‐caprolactone) (PCL) and poly(isobutylene) (PIB) blocks, connected by a specifically interacting hydrogen bond (thymine/2,6‐diaminotriazine). Starting from ring opening polymerization of ε‐caprolactone, the use of “click”‐chemistry enabled the introduction of thymine endgroups onto PCL polymer, thus generating the fully thymine‐substituted pure PCLs (1a, 1b) as judged via NMR and MALDI analysis. Physical mixing of 1a, 1b with a bivalent, bis(2,6‐diaminotriazine)‐containing molecule (2) generated the bivalent polymers BC1 and BC2, whereas mixing of 1a or 1b with the 2,6‐diaminotriazine‐substituted PIB (3) generated the supramolecular pseudo‐BCPs BC3 and BC4. Thermal investigations (DSC, Avrami analysis) revealed only minor changes in the crystallization behavior of BC1–BC4 with Avrami exponents close to three, indicative of a confluence of the growing crystals during the crystallization process. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011
• Aggregation and Chain Dynamics in Supramolecular Polymers by Dynamic Rheology: Cluster Formation and Self-Aggregation
  作者：Florian Herbst、Klaus Schröter、Ilja Gunkel、Stefan Gröger、Thomas Thurn-Albrecht、Jochen Balbach、Wolfgang H. Binder

  DOI：10.1021/ma101962y

  日期：2010.12.14

  chain ends with hydrogen-bonding units were prepared, and their association behavior in the melt state was investigated by dynamic rheology and compared to aggregation in solution, aiming at determining association dynamics in the solid state. A preparation combining living cationic polymerization with either azide/alkyne “click” reactions or nucleophilic substitution reactions enabled a full end group

  制备了带有氢键合单元的单官能和双官能链端的超分子聚异丁烯（PIB），并通过动态流变学研究了它们在熔融态下的缔合行为，并将其与溶液中的聚集进行了比较，旨在确定固态下的缔合动力学。将活性阳离子聚合与叠氮化物/炔烃“点击”反应或亲核取代反应结合在一起的制备方法，可以将完整的端基转化为最终的PIB聚合物，并用胸腺嘧啶或2,6-二氨基三嗪端基进行修饰，这已通过NMR和MALDI方法证明分子量约为3500至10000 g / mol。通过溶液共混制备这些具有特异性相互作用的胸腺嘧啶/三嗪部分的聚合物的化学计量混合物，并通过流变学测量研究温度依赖性动力学。在20-60°C的温度下，所有样品均显示出具有片状或部分交联结构的强热可逆聚集性，在〜80°C的温度下会发生聚集。由带有胸腺嘧啶和2，6-二氨基三嗪部分的各自双功能PIB形成具有桥联胶束结构的更复杂的聚集体。因此，除了特定的线性聚集体外，还必须考虑形成
• Hydrogen-bonded perylene/terthiophene-materials: synthesis and spectroscopic properties
  作者：Ali Shaygan Nia、Claudia Enders、Wolfgang H. Binder

  DOI：10.1016/j.tet.2011.10.096

  日期：2012.1

  The synthesis of layered donor/acceptor-materials based on perylenes (1a-c) and ter(thiophen)es (2a, 2b), ordered by hydrogen bonding moieties is reported. Based on the successful (selective) chlorination of 3,4:9,10-perylene tetracarboxylic dianhydride (3) to obtain a perylene derivative with only four chlorine atoms, subsequent functionalization with different hydrogen-bonding moieties is achieved via the azide/alkyne click reaction as proven by extensive ESI-TOF measurements. The perylene- (la-c) and terthiophene- (2a, 2b) compounds are useful as acceptor and donor parts, respectively, in organic solar cells as proven via UV vis and fluorescence measurements. Charge transfer between donor and acceptor parts (2a/1b) was determined as 41% via fluorescence resonance energy transfer (FRET), proving the association of the two components via the attached hydrogen bonding moieties. These measurements indicate that the mixture 2a/1b displays large potential for use as a layered ordered material with controlled spacings for organic solar cells based on a thereby facilitated charge-transfer. (C) 2011 Elsevier Ltd. All rights reserved.