BODIPY Compounds Substituted on Boron

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10495012" target="_blank" >RIV/00216208:11310/24:10495012 - isvavai.cz</a>

Výsledek na webu

<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=4Bzt3WIP.X" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=4Bzt3WIP.X</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3390/molecules29215157" target="_blank" >10.3390/molecules29215157</a>

Jazyk výsledku

angličtina

Název v původním jazyce

BODIPY Compounds Substituted on Boron

Popis výsledku v původním jazyce

BODIPY compounds are important organic dyes with exceptional spectral and photophysical properties and numerous applications in different scientific fields. Their widespread applications have flourished due to their easy structural modifications, which enable the preparation of different molecular structures with tunable spectral and photophysical properties. To date, researchers have mostly devoted their efforts to modifying BODIPY meso-position or pyrrole rings, whereas the substitution of fluorine atoms remains largely unexplored. However, chemistry of the boron atom is possible, and it enables tuning of the photophysical properties of the dyes, without tackling their spectral properties. Furthermore, modifications of boron affect the solubility and aggregation propensity of the molecules. This review article highlights methods for the preparation of 4-substituted compounds and the most important reactions on the boron of the BODIPY dyes. They were divided into reactions promoted by Lewis acid (AlCl3 or BCl3), or bases such as alkoxides and organometallic reagents. By using these two methodologies, it is possible to cleave B-F bonds and substitute them with B-C, B-N, or B-O bonds from different nucleophiles. A special emphasis in this review is given to still underdeveloped photochemical reactions of the boron atom of BODIPY dyes. These reactions have the potential to be used in the development of a new line of BODIPY photo-cleavable protective groups (also known as photocages) with bio-medicinal and photo-pharmacological applications, such as drug delivery.

Název v anglickém jazyce

BODIPY Compounds Substituted on Boron

Popis výsledku anglicky

BODIPY compounds are important organic dyes with exceptional spectral and photophysical properties and numerous applications in different scientific fields. Their widespread applications have flourished due to their easy structural modifications, which enable the preparation of different molecular structures with tunable spectral and photophysical properties. To date, researchers have mostly devoted their efforts to modifying BODIPY meso-position or pyrrole rings, whereas the substitution of fluorine atoms remains largely unexplored. However, chemistry of the boron atom is possible, and it enables tuning of the photophysical properties of the dyes, without tackling their spectral properties. Furthermore, modifications of boron affect the solubility and aggregation propensity of the molecules. This review article highlights methods for the preparation of 4-substituted compounds and the most important reactions on the boron of the BODIPY dyes. They were divided into reactions promoted by Lewis acid (AlCl3 or BCl3), or bases such as alkoxides and organometallic reagents. By using these two methodologies, it is possible to cleave B-F bonds and substitute them with B-C, B-N, or B-O bonds from different nucleophiles. A special emphasis in this review is given to still underdeveloped photochemical reactions of the boron atom of BODIPY dyes. These reactions have the potential to be used in the development of a new line of BODIPY photo-cleavable protective groups (also known as photocages) with bio-medicinal and photo-pharmacological applications, such as drug delivery.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Molecules

ISSN

1420-3049

e-ISSN

1420-3049

Svazek periodika

29

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

CH - Švýcarská konfederace

Počet stran výsledku

24

Strana od-do

5157

Kód UT WoS článku

001351808800001

EID výsledku v databázi Scopus

2-s2.0-85208555340