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; Marina RUSSO; Pauline STADLER; Patrick BREITENEDER; Guenther REDHAMMER; Markus HIMMELSBACH; Oliver BRUGGEMANN; Uwe MONKOWIUS; Petr KLÁN a Ian TEASDALE

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

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/21:00119421

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

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

Štítky

14313010, 143180, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 8. 6. 2025 10:14, 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

90121, velká výzkumná infrastruktura

Název: RECETOX RI

Přiložené soubory

1809778.pdf

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://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 = {https://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://doi.org/10.1039/d1py01245b.

Přehled o publikaci