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更高的BODIPY同系物——合成、反应性及光致发光研究。

Higher BODIPY Homologues-Synthesis, Reactivity, and Photoluminescence Investigations.

作者信息

Erlemeier Lukas, Richter Roman-Malte, Dunaj Tobias, Müller Marius J, Chatterjee Sangam, von Hänisch Carsten

机构信息

Department of Chemistry and Marburg Center for Quantum Materials and Sustainable Technology (mar.quest), Philipps University Marburg, Hans-Meerwein Straße 4, 35043, Marburg, Germany.

Institute of Experimental Physics I and Center for Materials Research, Justus Liebig University Giessen, 35392, Giessen, Germany.

出版信息

Chemistry. 2025 Jun 3;31(31):e202404764. doi: 10.1002/chem.202404764. Epub 2025 May 2.

DOI:10.1002/chem.202404764
PMID:40243188
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12133635/
Abstract

The synthesis of DPM group 13 (B─In, DPM = 1,5,9-trimesityldipyrromethene) compounds with halide substituents (Cl─I) is described. All compounds were fully characterized including NMR and IR spectroscopy as well as mass spectrometry. In addition, the solid state molecular structures have been determined by X-ray diffraction (XRD) analysis. As higher representatives of BODIPY (boron difluoride dipyrromethene) dyes, some of these DPM triel dihalides also exhibit an intense green fluorescence when exposed to sunlight. In this regard, the optical properties were investigated by UV/Vis and photoluminescence spectroscopy giving absorption maxima around 520 nm and fluorescence emission in the range between 550 and 660 nm. Fluorescence quantum efficiencies up to 42% could be obtained from measurements in toluene solution. Further, reactivity studies were carried out which opened-up access to mixed substituted DPM triels with one alkyl and one halide substituent.

摘要

描述了含卤化物取代基(Cl─I)的第13族DPM化合物(B─In,DPM = 1,5,9-三均三甲苯基二吡咯亚甲基)的合成。所有化合物均通过核磁共振、红外光谱以及质谱进行了全面表征。此外,通过X射线衍射(XRD)分析确定了固态分子结构。作为BODIPY(二氟化硼二吡咯亚甲基)染料的高级代表,其中一些DPM三价金属二卤化物在暴露于阳光时也会发出强烈的绿色荧光。在这方面,通过紫外/可见光谱和光致发光光谱对光学性质进行了研究,其吸收最大值约为520 nm,荧光发射范围在550至660 nm之间。在甲苯溶液中的测量可得到高达42%的荧光量子效率。此外,还进行了反应性研究,从而获得了具有一个烷基和一个卤化物取代基的混合取代DPM三价金属化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/c4d5ec6ecce5/CHEM-31-e202404764-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/89f919b4d494/CHEM-31-e202404764-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/d4f12402d090/CHEM-31-e202404764-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/46fea3794bf5/CHEM-31-e202404764-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/bd10a568e32f/CHEM-31-e202404764-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/31e8ec031c75/CHEM-31-e202404764-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/c73a1f0f5072/CHEM-31-e202404764-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/872350f2080b/CHEM-31-e202404764-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/a64d156062c1/CHEM-31-e202404764-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/c4d5ec6ecce5/CHEM-31-e202404764-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/89f919b4d494/CHEM-31-e202404764-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/d4f12402d090/CHEM-31-e202404764-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/46fea3794bf5/CHEM-31-e202404764-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/bd10a568e32f/CHEM-31-e202404764-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/31e8ec031c75/CHEM-31-e202404764-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/c73a1f0f5072/CHEM-31-e202404764-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/872350f2080b/CHEM-31-e202404764-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/a64d156062c1/CHEM-31-e202404764-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/266a/12133635/c4d5ec6ecce5/CHEM-31-e202404764-g004.jpg

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