Dataset Information

BCl₃-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

ABSTRACT: A general and straightforward method for the synthesis of COO-BODIPYs from F-BODIPYs and carboxylic acids is established. The method is based on the use of boron trichloride to activate the involved substitution of fluorine, which leads to high yields through rapid reactions under soft conditions. This mild method opens the way to unprecedented laser dyes with outstanding efficiencies and photostabilities, which are difficult to obtain by the current methods.

SUBMITTER: Ray C

PROVIDER: S-EPMC7272132 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Publications

BCl<sub>3</sub>-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

Ray César C Schad Christopher C Moreno Florencio F Maroto Beatriz L BL Bañuelos Jorge J Arbeloa Teresa T García-Moreno Inmaculada I Villafuerte Cassie C Muller Gilles G de la Moya Santiago S

The Journal of organic chemistry 20200317 7

A general and straightforward method for the synthesis of COO-BODIPYs from F-BODIPYs and carboxylic acids is established. The method is based on the use of boron trichloride to activate the involved substitution of fluorine, which leads to high yields through rapid reactions under soft conditions. This mild method opens the way to unprecedented laser dyes with outstanding efficiencies and photostabilities, which are difficult to obtain by the current methods. ...[more]

PMID: 32138513

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Project description:Icosahedral boron clusters-based BODIPY dyes represent a cutting-edge class of compounds that merge the unique properties of boron clusters with the exceptional fluorescence characteristics of BODIPY dyes. These kinds of molecules have garnered substantial interest due to their potential applications across various fields, mainly including optoelectronics, bioimaging, and potential use as boron carriers for Boron Neutron Capture Therapy (BNCT). Carborane clusters are known for their exceptional stability, rigid geometry, and 3D-aromaticity, while BODIPY dyes are renowned for their strong absorption, high fluorescence quantum yields, and photostability. The integration of carborane into BODIPY structures leverages the stability and versatility of carboranes while enhancing the photophysical properties of BODIPY-based fluorophores. This review explores the synthesis and structural diversity of boron clusters-based BODIPY dyes, highlighting how carborane incorporation can lead to significant changes in the electronic and optical properties of the dyes. We discuss the enhanced photophysical characteristics, such as red-shifted absorption and emission poperties, charge and electronic transfer effects, and improved cellular uptake, resulting from carborane substitution. The review also delves into the diverse applications of these compounds. In bioimaging, carborane-BODIPY dyes offer superior fluorescence properties and cellular internalization, making them ideal for cell tracking. In photodynamic therapy, (PDT) these dyes can act as potent photosensitizers capable of generating reactive oxygen species (ROS) for targeted cancer treatment making them excellent candidates for PDT. Additionally, their unique electronic properties make them suitable candidates for optoelectronic applications, including organic light-emitting diodes (OLEDs) and sensors. Overall, carborane-BODIPY dyes represent a versatile and promising class of materials with significant potential for innovation in scientific and technological applications. This review aims to provide a comprehensive overview of the current state of research on carborane-BODIPY dyes, highlighting their synthesis, properties, and broad application spectrum.

Dataset Information

BCl₃-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

Publications

BCl<sub>3</sub>-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

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Dataset Information

BCl3-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

Publications

BCl<sub>3</sub>-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.

Similar Datasets

OmicsDI is part of the ELIXIR infrastructure

Tweets

BCl₃-Activated Synthesis of COO-BODIPY Laser Dyes: General Scope and High Yields under Mild Conditions.