Metal-free synthesis, single crystal analysis and photophysical behavior of p-terphenyls

IF 4 2区化学 Q2 CHEMISTRY, PHYSICAL

Journal of Molecular Structure Pub Date : 2024-11-09 DOI:10.1016/j.molstruc.2024.140608

Sathish Kumar J, Fateh V. Singh

{"title":"Metal-free synthesis, single crystal analysis and photophysical behavior of p-terphenyls","authors":"Sathish Kumar J, Fateh V. Singh","doi":"10.1016/j.molstruc.2024.140608","DOIUrl":null,"url":null,"abstract":"<div><div>A simple and convenient metal-free approach for synthesizing p-terphenyls 7a–f is presented through a carbanion-induced ring transformation reaction involving 6-biphenyl-2H-pyran-2-ones 5 with pyruvic acetyl dimethyl aldehyde 6. Further the prepared dimethoxy p-terphenyls 7b-c,f were converted into diethoxy p-terphenyls 8a-c. The base-mediated ring transformation reactions proceeded smoothly under mild reaction conditions, resulting the formation of ring transformation products 7a-f and 8a-c in good to excellent yields. This synthetic approach allows the incorporation of both electron-withdrawing and electron-donating functionalities into p-terphenyl framework. Moreover, the structure of compound 7a was confirmed by its single crystal X-ray analysis. Additionally, the photophysical properties of synthesized p-terphenyls were analysed using UV-visible and fluorescence spectroscopy. Interestingly, the synthesized p-terphenyls 7a–f showed blue fluorescence in chloroform. The solvatochromic behaviour and concentration studies of compound 7d was also perforemd. Additionally, the thermal stability characteristics of compound 7d was also studied using TG and DTA analysis.</div></div>","PeriodicalId":16414,"journal":{"name":"Journal of Molecular Structure","volume":"1322 ","pages":"Article 140608"},"PeriodicalIF":4.0000,"publicationDate":"2024-11-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Molecular Structure","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0022286024031168","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, PHYSICAL","Score":null,"Total":0}

引用次数: 0

Abstract

A simple and convenient metal-free approach for synthesizing p-terphenyls 7a–f is presented through a carbanion-induced ring transformation reaction involving 6-biphenyl-2H-pyran-2-ones 5 with pyruvic acetyl dimethyl aldehyde 6. Further the prepared dimethoxy p-terphenyls 7b-c,f were converted into diethoxy p-terphenyls 8a-c. The base-mediated ring transformation reactions proceeded smoothly under mild reaction conditions, resulting the formation of ring transformation products 7a-f and 8a-c in good to excellent yields. This synthetic approach allows the incorporation of both electron-withdrawing and electron-donating functionalities into p-terphenyl framework. Moreover, the structure of compound 7a was confirmed by its single crystal X-ray analysis. Additionally, the photophysical properties of synthesized p-terphenyls were analysed using UV-visible and fluorescence spectroscopy. Interestingly, the synthesized p-terphenyls 7a–f showed blue fluorescence in chloroform. The solvatochromic behaviour and concentration studies of compound 7d was also perforemd. Additionally, the thermal stability characteristics of compound 7d was also studied using TG and DTA analysis.

查看原文本刊更多论文

对三联苯的无金属合成、单晶分析和光物理行为

通过 6-联苯-2H-吡喃-2-酮 5 与丙酮酸乙酰基二甲基醛 6 的碳离子诱导环转化反应，提出了一种简单方便的无金属对三联苯 7a-f 合成方法。制备的二甲氧基对三联苯 7b-c、f 进一步转化为二乙氧基对三联苯 8a-c。在温和的反应条件下，碱介导的环转化反应顺利进行，形成的环转化产物 7a-f 和 8a-c 收率良好甚至极佳。这种合成方法可以在对三联苯框架中同时加入抽电子官能团和供电子官能团。此外，化合物 7a 的结构已通过其单晶 X 射线分析得到证实。此外，还利用紫外可见光谱和荧光光谱分析了合成对三联苯的光物理特性。有趣的是，合成的对三联苯 7a-f 在氯仿中显示出蓝色荧光。此外，还对化合物 7d 的溶解变色行为和浓度进行了研究。此外，还使用 TG 和 DTA 分析法研究了化合物 7d 的热稳定性特征。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Molecular Structure 化学-物理化学

CiteScore

7.10

自引率

15.80%

发文量

2384

审稿时长

45 days

期刊介绍： The Journal of Molecular Structure is dedicated to the publication of full-length articles and review papers, providing important new structural information on all types of chemical species including: • Stable and unstable molecules in all types of environments (vapour, molecular beam, liquid, solution, liquid crystal, solid state, matrix-isolated, surface-absorbed etc.) • Chemical intermediates • Molecules in excited states • Biological molecules • Polymers. The methods used may include any combination of spectroscopic and non-spectroscopic techniques, for example: • Infrared spectroscopy (mid, far, near) • Raman spectroscopy and non-linear Raman methods (CARS, etc.) • Electronic absorption spectroscopy • Optical rotatory dispersion and circular dichroism • Fluorescence and phosphorescence techniques • Electron spectroscopies (PES, XPS), EXAFS, etc. • Microwave spectroscopy • Electron diffraction • NMR and ESR spectroscopies • Mössbauer spectroscopy • X-ray crystallography • Charge Density Analyses • Computational Studies (supplementing experimental methods) We encourage publications combining theoretical and experimental approaches. The structural insights gained by the studies should be correlated with the properties, activity and/ or reactivity of the molecule under investigation and the relevance of this molecule and its implications should be discussed.