Heterofunctional β-diketones incorporating ester linkages: Mesomorphism and solvatochromic effect

IF 5.3 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Liquids Pub Date : 2024-11-24 DOI:10.1016/j.molliq.2024.126572

U.V. Chervonova, N.G. Bichan, A.A. Ksenofontov, M.S. Gruzdev

引用次数: 0

Abstract

In this work a series of mesogens derived from 4-(4-octyloxybenzoyloxy)benzoic acid were synthesized and characterized. They acted as the main reagents in the Claisen condensation reaction to obtain a heterofunctional β-diketone containing both mesogenic long alkyloxybenzoic fragment and carbazole derivatives as chromophore unit in its structure. The results of the study of phase behavior showed that the synthesized elongated derivatives, including 4-(4-octyloxybenzoyloxy)benzoic acid as a key precursor for further modification, exhibit an enantiotropic mesomorphism, SmA and nematic mesophases, whereas the target β-diketone shows SmA mesophase only upon cooling from the isotropic melt. In addition, β-diketone demonstrates bright emission in the solvents of different polarity and in the solid state. The fluorescence quantum yield reaches values from 14 to 64 % depending on the nature of the solvent.

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含有酯连接的杂功能β-二酮类化合物：介形和溶色效应

在这项研究中，我们合成并鉴定了一系列由 4-(4-辛氧基苯甲酰氧基)苯甲酸衍生的中间体。它们在克莱森缩合反应中作为主要试剂，得到了一种杂官能团 β-二酮，其结构中同时含有介源长烷氧基苯甲酸片段和作为发色团单元的咔唑衍生物。相行为研究结果表明，合成的拉长衍生物（包括作为进一步改性关键前体的 4-(4-辛氧基苯甲酰氧基)苯甲酸）表现出对映各向同性的介构、SmA 介相和向列介相，而目标 β-二酮仅在从各向同性熔体冷却后才表现出 SmA 介相。此外，β-二酮在不同极性的溶剂中和固态下都会发出明亮的荧光。根据溶剂性质的不同，荧光量子产率可达 14% 到 64%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Molecular Liquids 化学-物理：原子、分子和化学物理

CiteScore

10.30

自引率

16.70%

发文量

2597

审稿时长

78 days

期刊介绍： The journal includes papers in the following areas: – Simple organic liquids and mixtures – Ionic liquids – Surfactant solutions (including micelles and vesicles) and liquid interfaces – Colloidal solutions and nanoparticles – Thermotropic and lyotropic liquid crystals – Ferrofluids – Water, aqueous solutions and other hydrogen-bonded liquids – Lubricants, polymer solutions and melts – Molten metals and salts – Phase transitions and critical phenomena in liquids and confined fluids – Self assembly in complex liquids.– Biomolecules in solution The emphasis is on the molecular (or microscopic) understanding of particular liquids or liquid systems, especially concerning structure, dynamics and intermolecular forces. The experimental techniques used may include: – Conventional spectroscopy (mid-IR and far-IR, Raman, NMR, etc.) – Non-linear optics and time resolved spectroscopy (psec, fsec, asec, ISRS, etc.) – Light scattering (Rayleigh, Brillouin, PCS, etc.) – Dielectric relaxation – X-ray and neutron scattering and diffraction. Experimental studies, computer simulations (MD or MC) and analytical theory will be considered for publication; papers just reporting experimental results that do not contribute to the understanding of the fundamentals of molecular and ionic liquids will not be accepted. Only papers of a non-routine nature and advancing the field will be considered for publication.