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首页> 外文期刊>Chemistry: A European journal >Organogel-hydrogel transformation by simple removal or inclusion of N-Boc-protection
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Organogel-hydrogel transformation by simple removal or inclusion of N-Boc-protection

机译：通过简单去除或包含N-Boc保护即可进行有机凝胶-水凝胶转化

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Development of organo- and hydrogelators is on the rise because of their extensive applications, from advanced materials to biomedicine. However, designing both types of gelator from a common structural scaffold is challenging, and becomes more significant if transformation between them can be achieved by a simple method. The present work reports the design and synthesis of both organo- and hydrogelators from amino acid/peptide-based amphiphilic precursors with a naphthyl group at the N terminus and a primary amine-containing hydrophilic ethyleneoxy unit at the C terminus. In alkaline medium, tert-butyloxycarbonyl (Boc) protection at the primary amine of the amphiphiles resulted in efficient organogelators (minimum-gelation concentration (MGC)=0.075-1.5%w/v). Interestingly, removal of the Boc protection from the ethyleneoxy unit, under acidic conditions, yielded amphiphiles capable of gelating water (MGC=0.9-3.0%w/v). Simple protection and deprotection chemistry was used to achieve transformation between the organogel and hydrogel by alteration of the pH. Combinations of different aliphatic and aromatic amino acids were investigated to discover their cumulative effect on the gelation properties. Field-emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM) were employed to investigate the supramolecular morphology of the thermoreversible gels. Spectroscopic investigations (FTIR, photoluminescence, XRD) revealed that noncovalent interactions, such as hydrogen bonding, π-π stacking, and van der Waals interactions play a decisive role in self-assembled gelation.
机译：由于从先进材料到生物医学的广泛应用，有机和水凝胶化剂的开发正在上升。然而，由共同的结构支架设计两种类型的胶凝剂是具有挑战性的，并且如果可以通过简单的方法实现它们之间的转化，则将变得更加重要。本工作报道了由N /末端带有萘基，C末端带有伯胺的亲水性乙氧基单元的基于氨基酸/肽的两亲性前体对有机和水凝胶化剂的设计和合成。在碱性介质中，两亲物伯胺上的叔丁氧羰基（Boc）保护可产生有效的有机胶凝剂（最小胶凝浓度（MGC）= 0.075-1.5％w / v）。有趣的是，在酸性条件下从乙氧基单元除去Boc保护基，得到能够凝胶化水的两亲物（MGC ＝ 0.9-3.0％w / v）。简单的保护和脱保护化学用于通过改变pH值来实现有机凝胶和水凝胶之间的转化。研究了不同脂肪族和芳香族氨基酸的组合，以发现它们对凝胶特性的累积影响。场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）被用来研究热可逆凝胶的超分子形态。光谱研究（FTIR，光致发光，XRD）显示非共价相互作用（例如氢键，π-π堆积和范德华相互作用）在自组装胶凝过程中起决定性作用。

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