Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes,Soft Matter

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Synthesis and organogelating behaviour of amino acid-functionalised triphenylenes
Soft Matter ( IF 2.9 ) Pub Date : 2017-07-26 00:00:00 , DOI: 10.1039/c7sm00676d
Jonathan E. Meegan _{1,

2,

3,

4} , Xiaofei Yang _{1,

2,

3,

4} , Ratana Rungsirisakun _{1,

2,

3,

4} , Sebastian C. Cosgrove _{1,

2,

3,

4} , Richard J. Bushby _{1,

2,

3,

4} , Amin Sadeghpour _{2,

3,

4,

5} , Michael Rappolt _{2,

3,

4,

5} , Rik Brydson _{2,

3,

4,

6} , Richard J. Ansell _{1,

2,

3,

4}

Affiliation

Four novel amino acid-functionalised triphenylenes have been prepared with glycine, L-alanine, L-phenylalanine and L-tryptophan ethyl ester side-chains. The glycine derivative is a good gelator of chloroform, the alanine derivative gels ethanol and toluene, and the phenylalanine derivative gels benzene and toluene. The tryptophan derivative does not gel any of the solvents tested, most probably due to its more bulky structure, but forms microspheres by evaporation-induced self-assembly. The self-assembly properties of the π-gelators have been investigated using infrared, UV-absorption and fluorescence spectroscopy, concentration- and temperature-dependent NMR, and X-ray scattering experiments on dried xerogel as well as the wet organogel. The latter experiments suggest the glycine gel in chloroform includes columnar aggregates, with an overall disordered columnar oblique mesophase. These compounds are of interest because of the well-known hole-transporting properties of triphenylene liquid crystals: 1-D columnar assemblies of these compounds may find applications in organic electronic devices.

中文翻译：

氨基酸官能化联苯的合成和有机胶凝行为

已经用甘氨酸，L-丙氨酸，L-苯丙氨酸和L制备了四种新颖的氨基酸官能化的亚苯撑。-色氨酸乙酯侧链。甘氨酸衍生物是氯仿的良好胶凝剂，丙氨酸衍生物使乙醇和甲苯胶凝，苯丙氨酸衍生物使苯和甲苯胶凝。色氨酸衍生物不会胶凝任何测试的溶剂，这很可能是由于其更大的结构，而是通过蒸发诱导的自组装形成微球。使用红外，紫外吸收和荧光光谱，浓度和温度相关的NMR，以及在干燥的干凝胶和湿有机凝胶上进行X射线散射实验，研究了π胶凝剂的自组装特性。后面的实验表明，氯仿中的甘氨酸凝胶包括柱状聚集体，整体呈无序的柱状斜中间相。

更新日期：2017-09-13

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