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Gelation-driven selection in dynamic covalent CC/CN exchange
Chemical Science ( IF 7.6 ) Pub Date : 2017-09-06 00:00:00 , DOI: 10.1039/c7sc02827j Chunshuang Liang 1, 2 , Sirinan Kulchat 1, 3 , Shimei Jiang 2, 4 , Jean-Marie Lehn 1
Chemical Science ( IF 7.6 ) Pub Date : 2017-09-06 00:00:00 , DOI: 10.1039/c7sc02827j Chunshuang Liang 1, 2 , Sirinan Kulchat 1, 3 , Shimei Jiang 2, 4 , Jean-Marie Lehn 1
Affiliation
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Knoevenagel barbiturate derivatives bearing long alkyl chains were proven to form organogels in suitable solvents based on supramolecular interactions. Their reaction with imines allows for component exchange through C![[double bond, length as m-dash]](http://www.rsc.org/images/entities/char_e001.gif)
C/CN recombination. The effect of various parameters (solvents, chain length, and temperature) on the CC/CN exchange reaction has been studied. Mixing Knoevenagel compound K and imine I-16 in a 1
:1 ratio generated a constitutional dynamic library containing the four constituents K, I-16, K′-16, and I′. The reversible exchange reaction was monitored by 1H-NMR, showing marked changes in the fractions of the four constituents on sol–gel interconversion as a function of temperature. The library composition changed from statistical distribution of the four constituents in the sol state to selective amplification of the gel forming K′-16 constituent together with that of its agonist I′. The process amounts to self-organization driven component selection in a constitutional dynamic organogel system undergoing gelation. This process displays up-regulation of the gel-forming constituent by component redistribution through reversible covalent connections.
中文翻译：
动态共价 CC/CN 交换中的凝胶驱动选择
基于超分子相互作用，具有长烷基链的 Knoevenagel 巴比妥酸盐衍生物已被证明在合适的溶剂中形成有机凝胶。它们与亚胺的反应允许通过 CC/C N 重组进行组分交换。研究了各种参数（溶剂、链长和温度）对 C C/C N 交换反应的影响。以 1 : 1 的比例混合 Knoevenagel 化合物K和亚胺I-16生成了一个包含四种成分K、I-16、K'-16和I'的组成动态库。可逆交换反应由1H-NMR，显示溶胶-凝胶相互转化中四种成分的分数随温度的显着变化。文库组成从溶胶状态的四种成分的统计分布变为凝胶形成K'-16成分及其激动剂I' 的选择性扩增。该过程相当于在进行凝胶化的构成动态有机凝胶系统中的自组织驱动组分选择。该过程通过可逆共价连接的组分重新分布显示凝胶形成成分的上调。
更新日期：2017-09-06
C/CN recombination. The effect of various parameters (solvents, chain length, and temperature) on the CC/CN exchange reaction has been studied. Mixing Knoevenagel compound K and imine I-16 in a 1:1 ratio generated a constitutional dynamic library containing the four constituents K, I-16, K′-16, and I′. The reversible exchange reaction was monitored by 1H-NMR, showing marked changes in the fractions of the four constituents on sol–gel interconversion as a function of temperature. The library composition changed from statistical distribution of the four constituents in the sol state to selective amplification of the gel forming K′-16 constituent together with that of its agonist I′. The process amounts to self-organization driven component selection in a constitutional dynamic organogel system undergoing gelation. This process displays up-regulation of the gel-forming constituent by component redistribution through reversible covalent connections.
中文翻译：
动态共价 CC/CN 交换中的凝胶驱动选择
基于超分子相互作用，具有长烷基链的 Knoevenagel 巴比妥酸盐衍生物已被证明在合适的溶剂中形成有机凝胶。它们与亚胺的反应允许通过 C
C/C N 重组进行组分交换。研究了各种参数（溶剂、链长和温度）对 C C/C N 交换反应的影响。以 1 : 1 的比例混合 Knoevenagel 化合物K和亚胺I-16生成了一个包含四种成分K、I-16、K'-16和I'的组成动态库。可逆交换反应由1H-NMR，显示溶胶-凝胶相互转化中四种成分的分数随温度的显着变化。文库组成从溶胶状态的四种成分的统计分布变为凝胶形成K'-16成分及其激动剂I' 的选择性扩增。该过程相当于在进行凝胶化的构成动态有机凝胶系统中的自组织驱动组分选择。该过程通过可逆共价连接的组分重新分布显示凝胶形成成分的上调。
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