The effect of terminal halogen atom on the self-assembly of bisthienylethene-based rod-like molecules

IF 2.2 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of the Iranian Chemical Society Pub Date : 2024-08-26 DOI:10.1007/s13738-024-03087-7
Ying Pu, Yurun Liang, Xiuning Hu, Guoyi Li, Binli Deng, Xiaotong Liu, Yulong Xiao
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Abstract

Three novel rod-like molecules containing a bisthienylethene as π-conjugate rigid core with a different type of terminal functional atom (H, Cl, Br) were constructed by using Suzuki coupling and Knoevenagel reactions. The effect of the terminal functional atom on self-assembly behaviors in both bulk state and solution states and solid structures was investigated by using differential scanning calorimetry, polarized optical microscopy, small-angle X-ray scattering diffraction, density functional theory calculations and field-emission scanning electron microscopy. The non-halogen substituted compound and chlorinated compound are non-mesogen, whereas the brominated compound can self-assemble into a monotropic single-layer smectic A phase. The non-halogen substituted compound cannot form organogel in the common organic solvents, the chlorinated compound can form yellow-green fluorescent oragnogels in ethyl acetate and acetone, with rod-like morphology and brominated compound can form yellow-green, yellow or orange fluorescent oragnogels in ethyl acetate, acetone, 1,4-dioxane and toluene with sheet-like morphology. In addition, the terminal halogen atom induced great changes in the orderliness of solid morphology. Therefore, tuning terminal halogen atom could well lead to the transition of self-assembly behaviors in bulk state and solution state, which provides a way to obtain different self-assembly materials.

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末端卤素原子对双噻吩基棒状分子自组装的影响
利用铃木偶联反应和克诺文纳格尔反应,构建了三种新型棒状分子,它们以双噻吩为π-共轭刚性核心,具有不同类型的末端官能团(H、Cl、Br)。利用差示扫描量热法、偏振光学显微镜、小角 X 射线散射衍射、密度泛函理论计算和场发射扫描电子显微镜研究了末端官能团原子对体态和溶液态自组装行为以及固体结构的影响。非卤素取代的化合物和氯化化合物都是非介质,而溴化化合物则可以自组装成单向性的单层 Smectic A 相。非卤素取代的化合物不能在普通有机溶剂中形成有机凝胶,氯化化合物可在乙酸乙酯和丙酮中形成具有杆状形态的黄绿色荧光有机凝胶,溴化化合物可在乙酸乙酯、丙酮、1,4-二氧六环和甲苯中形成具有片状形态的黄绿色、黄色或橙色荧光有机凝胶。此外,末端卤素原子会导致固体形态的有序性发生巨大变化。因此,调整末端卤素原子可以很好地导致体态和溶液态自组装行为的转变,为获得不同的自组装材料提供了途径。
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来源期刊
CiteScore
4.40
自引率
8.30%
发文量
230
审稿时长
5.6 months
期刊介绍: JICS is an international journal covering general fields of chemistry. JICS welcomes high quality original papers in English dealing with experimental, theoretical and applied research related to all branches of chemistry. These include the fields of analytical, inorganic, organic and physical chemistry as well as the chemical biology area. Review articles discussing specific areas of chemistry of current chemical or biological importance are also published. JICS ensures visibility of your research results to a worldwide audience in science. You are kindly invited to submit your manuscript to the Editor-in-Chief or Regional Editor. All contributions in the form of original papers or short communications will be peer reviewed and published free of charge after acceptance.
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