Highly efficient one-pot three-component synthesis of novel organoboron markers for diesel fuel

IF 5.7 3区材料科学 Q2 MATERIALS SCIENCE, MULTIDISCIPLINARY

Materials Research Bulletin Pub Date : 2025-07-18 DOI:10.1016/j.materresbull.2025.113668

Nereida S. Campos-Medellín , Rosa M. Jiménez-Barrera , Horacio Reyes-Pérez , Emanuel Bojórquez-Quíntal , Eugenio Hernández-Fernández , Abner Esperanza-Norzagaray , Rodrigo Chan-Navarro , María C. García-López

{"title":"Highly efficient one-pot three-component synthesis of novel organoboron markers for diesel fuel","authors":"Nereida S. Campos-Medellín , Rosa M. Jiménez-Barrera , Horacio Reyes-Pérez , Emanuel Bojórquez-Quíntal , Eugenio Hernández-Fernández , Abner Esperanza-Norzagaray , Rodrigo Chan-Navarro , María C. García-López","doi":"10.1016/j.materresbull.2025.113668","DOIUrl":null,"url":null,"abstract":"<div><div>In the present work, four fluorescent organoboron esters have been prepared by a fast self-assembly-assisted synthesis, achieved in short reaction time. The resulting organoboron esters were elucidated by <sup>1</sup>H and <sup>11</sup>B NMR, as well as mass spectrometry, and for <strong>3</strong> was further confirmed by single-crystal diffraction method, where the solved crystal structure shows a tetracoordinate boron atom with a distorted tetrahedral geometry. The photophysical behavior of all derivatives was analyzed in a fresh solution, demonstrating the presence of negative solvatochromism. Additionally, phenylboronic acid derivative 2, featuring <em>tert</em>‑butyl groups, demonstrated superior photostability compared to their derivatives. Mass spectrometry analysis also indicated energetic stability of the molecular ion of compound <strong>4</strong>. Notably, compound <strong>2</strong> exhibited good solubility, high photostability, thermal decomposition above 200 °C and adequate emissive properties, making it a promising fluorescent dye for fuel marking applications. Its exceptional photostability, positions molecule <strong>2</strong> as a promising candidate for fuel marker applications.</div></div>","PeriodicalId":18265,"journal":{"name":"Materials Research Bulletin","volume":"193 ","pages":"Article 113668"},"PeriodicalIF":5.7000,"publicationDate":"2025-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Materials Research Bulletin","FirstCategoryId":"88","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0025540825003757","RegionNum":3,"RegionCategory":"材料科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"MATERIALS SCIENCE, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

Abstract

In the present work, four fluorescent organoboron esters have been prepared by a fast self-assembly-assisted synthesis, achieved in short reaction time. The resulting organoboron esters were elucidated by ¹H and ¹¹B NMR, as well as mass spectrometry, and for 3 was further confirmed by single-crystal diffraction method, where the solved crystal structure shows a tetracoordinate boron atom with a distorted tetrahedral geometry. The photophysical behavior of all derivatives was analyzed in a fresh solution, demonstrating the presence of negative solvatochromism. Additionally, phenylboronic acid derivative 2, featuring tert‑butyl groups, demonstrated superior photostability compared to their derivatives. Mass spectrometry analysis also indicated energetic stability of the molecular ion of compound 4. Notably, compound 2 exhibited good solubility, high photostability, thermal decomposition above 200 °C and adequate emissive properties, making it a promising fluorescent dye for fuel marking applications. Its exceptional photostability, positions molecule 2 as a promising candidate for fuel marker applications.

Abstract Image

查看原文本刊更多论文

新型柴油用有机硼标记物的高效一锅三组分合成

在本工作中，通过快速自组装辅助合成，在短反应时间内制备了四种荧光有机硼酯。所得有机硼酯经1H、11B核磁共振及质谱分析确证，并通过单晶衍射法进一步确证了其中的3，解得的晶体结构为一个扭曲四面体形状的四配位硼原子。在新鲜溶液中分析了所有衍生物的光物理行为，证明存在负溶剂变色。此外，苯硼酸衍生物2具有叔丁基，与它们的衍生物相比，表现出优越的光稳定性。质谱分析还表明化合物4的分子离子具有能量稳定性。值得注意的是，化合物2具有良好的溶解度，高光稳定性，在200°C以上热分解和足够的发射特性，使其成为一种有前途的燃料标记荧光染料。它具有优异的光稳定性，使分子2成为燃料标记应用的有前途的候选者。

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

Materials Research Bulletin 工程技术-材料科学：综合

CiteScore

9.80

自引率

5.60%

发文量

372

审稿时长

42 days

期刊介绍： Materials Research Bulletin is an international journal reporting high-impact research on processing-structure-property relationships in functional materials and nanomaterials with interesting electronic, magnetic, optical, thermal, mechanical or catalytic properties. Papers purely on thermodynamics or theoretical calculations (e.g., density functional theory) do not fall within the scope of the journal unless they also demonstrate a clear link to physical properties. Topics covered include functional materials (e.g., dielectrics, pyroelectrics, piezoelectrics, ferroelectrics, relaxors, thermoelectrics, etc.); electrochemistry and solid-state ionics (e.g., photovoltaics, batteries, sensors, and fuel cells); nanomaterials, graphene, and nanocomposites; luminescence and photocatalysis; crystal-structure and defect-structure analysis; novel electronics; non-crystalline solids; flexible electronics; protein-material interactions; and polymeric ion-exchange membranes.