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A Low-Molecular-Weight Gelator Composed of Pyrene and Fluorene Moieties for Effective Charge Transfer in Supramolecular Ambidextrous Gel
Langmuir ( IF 3.7 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1021/acs.langmuir.7b03453 Samala Murali Mohan Reddy 1 , Pramod Dorishetty 2 , George Augustine , Abhijit P. Deshpande 2 , Niraikulam Ayyadurai , Ganesh Shanmugam 1
Langmuir ( IF 3.7 ) Pub Date : 2017-11-14 00:00:00 , DOI: 10.1021/acs.langmuir.7b03453 Samala Murali Mohan Reddy 1 , Pramod Dorishetty 2 , George Augustine , Abhijit P. Deshpande 2 , Niraikulam Ayyadurai , Ganesh Shanmugam 1
Affiliation
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Charge-transfer (CT) gel materials obtained from low-molecular-weight (LMW) compounds through a supramolecular self-assembly approach have received fascinating attention by many researchers because of their interesting material property and potential applications. However, most of the CT gel materials constructed were of organogels while the construction of CT gels in the form of a hydrogel is a challenge because of the solubility issue in water, which considerably limits the use of CT hydrogels. Herein, for the first time, we report a new LMW gelator [Nα-(fluorenylmethoxycarbonyl)-Nε-(δ-butyric-1-pyrenyl)-l-lysine, (FmKPy)], composed of two functional moieties such as fluorenylmethoxycarbonyl and pyrene, which not only parade both hydro and organo (ambidextrous) supramolecular gel formation but also exhibit CT ambidextrous gels when mixed with an electron acceptor such as 2,4,7-trinitro-9-fluorenone (TNF). This finding is significant as the established CT organogelator in the literature did not form an organogel in the absence of an electron acceptor or lose their gelation property upon the addition of the acceptor. CT between pyrene and TNF was confirmed by the color change as well as the appearance of the CT band in the visible region of the absorption spectrum. CT between FmKPy and TNF was supported by the solvent dilution method using tetrahydrofuran as the gel breaker and pyrene fluorescence quenching in the case compound containing pyrene and TNF. The morphology of FmKPy ambidextrous gels indicates the fibrous nature while the self-assembled structure is primarily stabilized by π–π stacking among fluorenyl and pyrenyl moieties and hydrogen bonding between amide groups. The FmKPy–TNF CT ambidextrous gel retains the fibrous nature; however, the size of the fibers changed. In FmKPy–TNF CT gels, TNF is intercalated between pyrene moieties in the self-assembled structure as confirmed by fluorescence quenching and powder X-ray diffraction. The FmKPy ambidextrous gel exhibits significant properties such as low minimum gelation concentration (MGC), thixotropic nature, pH stimuli response, and high thermal stability. Upon the addition of TNF, the FmKPy–TNF CT ambidextrous gel maintains all these properties except MGC which increased for FmKPy–TNF. Because pyrene-based LMW organogels have been developed widely for many applications while their hydrogels were limited, the current finding of the pyrene-based ambidextrous fluorescent gel with the CT property provides a wide opportunity to use FmKPy as a soft material maker and also for potential applications in fields like surface coating, three-dimensional printing, and so forth.
中文翻译：
一种由and和芴部分组成的低分子量胶凝剂，用于超分子双足凝胶中的有效电荷转移
通过超分子自组装方法从低分子量（LMW）化合物获得的电荷转移（CT）凝胶材料因其有趣的材料特性和潜在应用而受到了许多研究人员的关注。然而，构造的大多数CT凝胶材料是有机凝胶，而水凝胶形式的CT凝胶的构造由于在水中的溶解度问题而受到挑战，这大大限制了CT水凝胶的使用。这里，对于第一次，我们报告一个新LMW胶凝剂[ Ñ α - （芴） - ñ ε - （δ -丁-1-芘基） -升-赖氨酸（（FmKPy）]，由两个功能部分组成，例如芴基甲氧基羰基和pyr，它们不仅与水和有机（灵巧的）超分子凝胶形成共存，而且在与电子受体（如2,4）混合时也呈现出CT灵巧的凝胶。 ，7-三硝基-9-芴酮（TNF）。该发现是重要的，因为在文献中已建立的CT有机胶凝剂在没有电子受体的情况下没有形成有机凝胶，或者在加入受体时失去了其胶凝性质。the和TNF之间的CT可以通过颜色变化以及在吸收光谱的可见区域中出现的CT谱带来确认。FmKPy和TNF之间的CT通过溶剂稀释法得到支持，该方法使用四氢呋喃作为破胶剂，并且在含有containing和TNF的化合物的情况下进行pyr荧光猝灭。FmKPy灵巧凝胶的形态表明其纤维性质，而自组装结构主要通过芴基和pyr基部分之间的π-π堆积和酰胺基团之间的氢键稳定。FmKPy-TNF CT双歧杆菌凝胶保留了纤维性质。但是，纤维的尺寸发生了变化。在FmKPy-TNF CT凝胶中，通过荧光猝灭和粉末X射线衍射证实，TNF插入自组装结构中的pyr部分之间。FmKPy灵巧凝胶表现出显着的特性，例如较低的最低胶凝浓度（MGC），触变性，pH刺激响应，以及高的热稳定性。加入TNF后，FmKPy-TNF CT的灵巧凝胶保持了所有这些特性，但MGC随FmKPy-TNF的增加而增加。由于pyr基LMW有机凝胶在水凝胶有限的情况下已广泛用于许多应用，因此具有CT特性的the基双歧荧光凝胶的当前发现为将FmKPy用作软质材料制造商提供了广阔的机会，同时也具有潜在的应用前景。在表面涂层，三维印刷等领域中的应用。
更新日期：2017-11-14
中文翻译：
一种由and和芴部分组成的低分子量胶凝剂，用于超分子双足凝胶中的有效电荷转移
通过超分子自组装方法从低分子量（LMW）化合物获得的电荷转移（CT）凝胶材料因其有趣的材料特性和潜在应用而受到了许多研究人员的关注。然而，构造的大多数CT凝胶材料是有机凝胶，而水凝胶形式的CT凝胶的构造由于在水中的溶解度问题而受到挑战，这大大限制了CT水凝胶的使用。这里，对于第一次，我们报告一个新LMW胶凝剂[ Ñ α - （芴） - ñ ε - （δ -丁-1-芘基） -升-赖氨酸（（FmKPy）]，由两个功能部分组成，例如芴基甲氧基羰基和pyr，它们不仅与水和有机（灵巧的）超分子凝胶形成共存，而且在与电子受体（如2,4）混合时也呈现出CT灵巧的凝胶。 ，7-三硝基-9-芴酮（TNF）。该发现是重要的，因为在文献中已建立的CT有机胶凝剂在没有电子受体的情况下没有形成有机凝胶，或者在加入受体时失去了其胶凝性质。the和TNF之间的CT可以通过颜色变化以及在吸收光谱的可见区域中出现的CT谱带来确认。FmKPy和TNF之间的CT通过溶剂稀释法得到支持，该方法使用四氢呋喃作为破胶剂，并且在含有containing和TNF的化合物的情况下进行pyr荧光猝灭。FmKPy灵巧凝胶的形态表明其纤维性质，而自组装结构主要通过芴基和pyr基部分之间的π-π堆积和酰胺基团之间的氢键稳定。FmKPy-TNF CT双歧杆菌凝胶保留了纤维性质。但是，纤维的尺寸发生了变化。在FmKPy-TNF CT凝胶中，通过荧光猝灭和粉末X射线衍射证实，TNF插入自组装结构中的pyr部分之间。FmKPy灵巧凝胶表现出显着的特性，例如较低的最低胶凝浓度（MGC），触变性，pH刺激响应，以及高的热稳定性。加入TNF后，FmKPy-TNF CT的灵巧凝胶保持了所有这些特性，但MGC随FmKPy-TNF的增加而增加。由于pyr基LMW有机凝胶在水凝胶有限的情况下已广泛用于许多应用，因此具有CT特性的the基双歧荧光凝胶的当前发现为将FmKPy用作软质材料制造商提供了广阔的机会，同时也具有潜在的应用前景。在表面涂层，三维印刷等领域中的应用。
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