Green-light photocleavable meso-methyl BODIPY building blocks
for macromolecular chemistry

J 2021

Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry

STRASSER, Paul, Marina RUSSO, Pauline STADLER, Patrick BREITENEDER, Guenther REDHAMMER et. al.

Základní údaje

Originální název

Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry

Autoři

STRASSER, Paul (40 Rakousko), Marina RUSSO (380 Itálie, domácí), Pauline STADLER (40 Rakousko), Patrick BREITENEDER (40 Rakousko), Guenther REDHAMMER (40 Rakousko), Markus HIMMELSBACH (40 Rakousko), Oliver BRUGGEMANN (40 Rakousko), Uwe MONKOWIUS (40 Rakousko), Petr KLÁN (203 Česká republika, garant, domácí) a Ian TEASDALE (40 Rakousko)

Vydání

POLYMER CHEMISTRY, Royal Society of Chemistry, 2021, 1759-9954

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10404 Polymer science

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 5.364

Kód RIV

RIV/00216224:14310/21:00119421

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1039/d1py01245b

UT WoS

000721517000001

Klíčová slova anglicky

PHOTOREMOVABLE PROTECTING GROUPS; PHOTOPROTECTING GROUPS; POLYMER; DERIVATIVES; REACTIVITY; COPOLYMER; MICELLES; RELEASE

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 17. 2. 2023 21:14, Mgr. Michaela Hylsová, Ph.D.

Anotace

V originále

We report the design of easily accessible, photocleavable meso-methyl BODIPY monomers suitably functionalised for incorporation into macromolecules. Firstly a BODIPY-diol as a novel AA-type bifunctional monomer is reported. Secondly, from the same common BODIPY precursor, a clickable, azide functionalised AB-type hetero-bifunctional monomer was prepared. Photochemical studies of model compounds confirmed the ability of these compounds to undergo photocleavage in green light (lambda > 500 nm). Their usefulness for photoclippable macromolecular systems is then demonstrated: firstly by incorporating the diols into polyurethane hydrogels shown to undergo photocleavage and hence dissolution under visible light irradiation and secondly, the preparation of water-soluble macromolecular photocages able to photorelease small molecules. Thus the results presented herein describe a proof-of-principle for BODIPY-based photoresponsive materials, for example, for use as degradable polymers, sacrificial materials for lithography or for the delivery of caged pharmaceuticals.

Návaznosti

EF17_043/0009632, projekt VaV

Název: CETOCOEN Excellence

GA21-01799S, projekt VaV

Název: Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

Investor: Grantová agentura ČR, Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

LM2018121, projekt VaV

Název: Výzkumná infrastruktura RECETOX (Akronym: RECETOX RI)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX RI

Přiložené soubory

1809778.pdf

Vyhledat podobné dokumenty

Citovat

STRASSER, Paul, Marina RUSSO, Pauline STADLER, Patrick BREITENEDER, Guenther REDHAMMER, Markus HIMMELSBACH, Oliver BRUGGEMANN, Uwe MONKOWIUS, Petr KLÁN a Ian TEASDALE. Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry. POLYMER CHEMISTRY. Royal Society of Chemistry, 2021, roč. 12, č. 47, s. 6927-6936. ISSN 1759-9954. Dostupné z: https://dx.doi.org/10.1039/d1py01245b.

@article{1809778,
   author = {Strasser, Paul and Russo, Marina and Stadler, Pauline and Breiteneder, Patrick and Redhammer, Guenther and Himmelsbach, Markus and Bruggemann, Oliver and Monkowius, Uwe and Klán, Petr and Teasdale, Ian},
   article_number = {47},
   doi = {http://dx.doi.org/10.1039/d1py01245b},
   keywords = {PHOTOREMOVABLE PROTECTING GROUPS; PHOTOPROTECTING GROUPS; POLYMER; DERIVATIVES; REACTIVITY; COPOLYMER; MICELLES; RELEASE},
   language = {eng},
   issn = {1759-9954},
   journal = {POLYMER CHEMISTRY},
   title = {Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry},
   url = {https://pubs.rsc.org/en/content/articlelanding/2021/PY/D1PY01245B},
   volume = {12},
   year = {2021}
}

TY  - JOUR
ID  - 1809778
AU  - Strasser, Paul - Russo, Marina - Stadler, Pauline - Breiteneder, Patrick - Redhammer, Guenther - Himmelsbach, Markus - Bruggemann, Oliver - Monkowius, Uwe - Klán, Petr - Teasdale, Ian
PY  - 2021
TI  - Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry
JF  - POLYMER CHEMISTRY
VL  - 12
IS  - 47
SP  - 6927-6936
EP  - 6927-6936
PB  - Royal Society of Chemistry
SN  - 17599954
KW  - PHOTOREMOVABLE PROTECTING GROUPS
KW  - PHOTOPROTECTING GROUPS
KW  - POLYMER
KW  - DERIVATIVES
KW  - REACTIVITY
KW  - COPOLYMER
KW  - MICELLES
KW  - RELEASE
UR  - https://pubs.rsc.org/en/content/articlelanding/2021/PY/D1PY01245B
N2  - We report the design of easily accessible, photocleavable meso-methyl BODIPY monomers suitably functionalised for incorporation into macromolecules. Firstly a BODIPY-diol as a novel AA-type bifunctional monomer is reported. Secondly, from the same common BODIPY precursor, a clickable, azide functionalised AB-type hetero-bifunctional monomer was prepared. Photochemical studies of model compounds confirmed the ability of these compounds to undergo photocleavage in green light (lambda > 500 nm). Their usefulness for photoclippable macromolecular systems is then demonstrated: firstly by incorporating the diols into polyurethane hydrogels shown to undergo photocleavage and hence dissolution under visible light irradiation and secondly, the preparation of water-soluble macromolecular photocages able to photorelease small molecules. Thus the results presented herein describe a proof-of-principle for BODIPY-based photoresponsive materials, for example, for use as degradable polymers, sacrificial materials for lithography or for the delivery of caged pharmaceuticals.
ER  -

STRASSER, Paul, Marina RUSSO, Pauline STADLER, Patrick BREITENEDER, Guenther REDHAMMER, Markus HIMMELSBACH, Oliver BRUGGEMANN, Uwe MONKOWIUS, Petr KLÁN a Ian TEASDALE. Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry. \textit{POLYMER CHEMISTRY}. Royal Society of Chemistry, 2021, roč.~12, č.~47, s.~6927-6936. ISSN~1759-9954. Dostupné z: https://dx.doi.org/10.1039/d1py01245b.

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