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基于硼二吡咯甲烷染料-香豆素二联体的分子转子的快速访问-具有宽带吸收。

Ready Access to Molecular Rotors Based on Boron Dipyrromethene Dyes-Coumarin Dyads Featuring Broadband Absorption.

机构信息

Departamento de Química, Universidad de Guanajuato. Noria Alta S/N. Guanajuato, Gto. 36050, Mexico.

Departamento de Química Física. Universidad del País Vasco-EHU, Apartado 644, 48080 Bilbao, Spain.

出版信息

Molecules. 2020 Feb 12;25(4):781. doi: 10.3390/molecules25040781.

DOI:10.3390/molecules25040781
PMID:32059435
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7070740/
Abstract

Herein we report on a straightforward access method for boron dipyrromethene dyes (BODIPYs)-coumarin hybrids linked through their respective 8- and 6- positions, with wide functionalization of the coumarin fragment, using salicylaldehyde as a versatile building block. The computationally-assisted photophysical study unveils broadband absorption upon proper functionalization of the coumarin, as well as the key role of the conformational freedom of the coumarin appended at the position of the BODIPY. Such free motion almost suppresses the fluorescence signal, but enables us to apply these dyads as molecular rotors to monitor the surrounding microviscosity.

摘要

在此，我们报告了一种通过各自的 8 位和 6 位连接硼二吡咯甲川染料（BODIPY）-香豆素杂化物的简便方法，使用水杨醛作为多功能构建块，对香豆素片段进行广泛的功能化。通过对香豆素进行适当的功能化，计算辅助的光物理研究揭示了宽带吸收，以及 BODIPY 上的 位连接的香豆素的构象自由度的关键作用。这种自由运动几乎抑制了荧光信号，但使我们能够将这些偶联物用作分子转子来监测周围的微粘度。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/fa619caae6de/molecules-25-00781-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/894335505bd0/molecules-25-00781-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/94137a702228/molecules-25-00781-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/56d244ff1676/molecules-25-00781-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/ee18b8943e4d/molecules-25-00781-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/fcd0e115c8e1/molecules-25-00781-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/7e428d744376/molecules-25-00781-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/de46424e9f31/molecules-25-00781-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/c12a06ba6930/molecules-25-00781-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/a2b329f6249a/molecules-25-00781-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/fa619caae6de/molecules-25-00781-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/894335505bd0/molecules-25-00781-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/94137a702228/molecules-25-00781-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/56d244ff1676/molecules-25-00781-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/ee18b8943e4d/molecules-25-00781-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/fcd0e115c8e1/molecules-25-00781-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/7e428d744376/molecules-25-00781-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/de46424e9f31/molecules-25-00781-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/c12a06ba6930/molecules-25-00781-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/a2b329f6249a/molecules-25-00781-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0dd1/7070740/fa619caae6de/molecules-25-00781-g006.jpg

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本文引用的文献

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Front Chem. 2019 Nov 26;7:825. doi: 10.3389/fchem.2019.00825. eCollection 2019.
2
Photophysical properties of some novel tetraphenylimidazole derived BODIPY based fluorescent molecular rotors.一些新型四苯并咪唑衍生的 BODIPY 基荧光分子转子的光物理性质。
Dalton Trans. 2020 Jan 2;49(2):438-452. doi: 10.1039/c9dt04177j.
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Recent Progress of BODIPY Dyes With Aggregation-Induced Emission.具有聚集诱导发光特性的BODIPY染料的研究进展
Front Chem. 2019 Oct 25;7:712. doi: 10.3389/fchem.2019.00712. eCollection 2019.
4
Regioisomeric BODIPY Benzodithiophene Dyads and Triads with Tunable Red Emission as Ratiometric Temperature and Viscosity Sensors.具有可调谐红光发射的区域异构体 BODIPY 苯并二噻吩二聚体和三聚体作为比率型温度和粘度传感器。
Chemistry. 2019 Nov 22;25(65):14870-14880. doi: 10.1002/chem.201902952. Epub 2019 Oct 28.
5
Comparative study of two near-infrared coumarin-BODIPY dyes for bioimaging and photothermal therapy of cancer.两种近红外香豆素-BODIPY 染料用于癌症的生物成像和光热治疗的对比研究。
J Mater Chem B. 2019 Jul 31;7(30):4717-4724. doi: 10.1039/c9tb01165j.
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A broadband and strong visible-light-absorbing photosensitizer boosts hydrogen evolution.一种宽带且强可见光吸收的光敏剂促进析氢。
Nat Commun. 2019 Jul 17;10(1):3155. doi: 10.1038/s41467-019-11099-8.
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Tuning Photoinduced Electron Transfer Efficiency of Fluorogenic BODIPY-α-Tocopherol Analogues.调控荧光 BODIPY-α-生育酚类似物的光诱导电子转移效率。
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