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调节BODIPY染料的光物理性质并通过氢键研究其自组装

Tuning the Photophysical Properties of BODIPY Dyes and Studying Their Self-Assembly via Hydrogen Bonding.

作者信息

Akyol Büşra, Çokluk Eylül Merve, Ayhan Mehmet Menaf, Tuncel Kostakoğlu Sinem, Gürek Ayşe Gül

机构信息

Department of Chemistry Gebze Technical University, Gebze Kocaeli 41400, Turkey.

出版信息

ACS Omega. 2024 Dec 27;10(1):1716-1726. doi: 10.1021/acsomega.4c09745. eCollection 2025 Jan 14.

DOI:10.1021/acsomega.4c09745
PMID:39829528
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11740828/
Abstract

Here, BODIPY derivatives were functionalized with barbituric acid, which has multiple hydrogen bonding abilities that are directional, to have highly ordered hydrogen bond-mediated self-assembled structures to tune BODIPY's photophysical properties. The synthesis of barbituric acid-functionalized BODIPY derivatives via Vilsmeier and Knoevenagel reactions was achieved, and the resulting compounds were characterized with FT-IR, H NMR, C NMR spectroscopy, and mass spectrometry. Hydrogen bond-mediated self-assembled structures were investigated through UV-vis and fluorescence spectrophotometry, H NMR spectroscopy, and a dynamic light scattering method in solution. Moreover, SEM, HR-TEM, and PXRD were used to study the self-assembly of compounds in bulk.

摘要

在这里，用具有多个定向氢键能力的巴比妥酸对BODIPY衍生物进行功能化，以形成高度有序的氢键介导的自组装结构，从而调节BODIPY的光物理性质。通过Vilsmeier反应和Knoevenagel反应实现了巴比妥酸功能化的BODIPY衍生物的合成，并用傅里叶变换红外光谱（FT-IR）、氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）光谱和质谱对所得化合物进行了表征。通过紫外-可见光谱和荧光分光光度法、¹H NMR光谱以及溶液中的动态光散射法研究了氢键介导的自组装结构。此外，还使用扫描电子显微镜（SEM）、高分辨透射电子显微镜（HR-TEM）和粉末X射线衍射（PXRD）研究了化合物在本体中的自组装。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/4031b9547857/ao4c09745_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/f1bbf079cd5a/ao4c09745_0009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/522ee0f0ed75/ao4c09745_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/6de156cdf0ff/ao4c09745_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/2e9732cd0c7a/ao4c09745_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/4031b9547857/ao4c09745_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/f1bbf079cd5a/ao4c09745_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/dd1dcdabf2cd/ao4c09745_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/d0aa99673ba4/ao4c09745_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/49fc9eb24a2f/ao4c09745_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/78b7daab92c6/ao4c09745_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/522ee0f0ed75/ao4c09745_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/6de156cdf0ff/ao4c09745_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/2e9732cd0c7a/ao4c09745_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/14bf/11740828/4031b9547857/ao4c09745_0008.jpg

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本文引用的文献

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