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.

Basic information

Original name

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

Authors

STRASSER, Paul (40 Austria), Marina RUSSO (380 Italy, belonging to the institution), Pauline STADLER (40 Austria), Patrick BREITENEDER (40 Austria), Guenther REDHAMMER (40 Austria), Markus HIMMELSBACH (40 Austria), Oliver BRUGGEMANN (40 Austria), Uwe MONKOWIUS (40 Austria), Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution) and Ian TEASDALE (40 Austria)

Edition

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

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10404 Polymer science

Country of publisher

United Kingdom of Great Britain and Northern Ireland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.364

RIV identification code

RIV/00216224:14310/21:00119421

Organization unit

Faculty of Science

DOI

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

UT WoS

000721517000001

Keywords in English

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

Abstract

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.

Links

EF17_043/0009632, research and development project

Name: CETOCOEN Excellence

GA21-01799S, research and development project

Name: Flavonoidy jako unikátní třída molekul fotochemicky uvolňujících oxid uhelnatý

Investor: Czech Science Foundation

LM2018121, research and development project

Name: Výzkumná infrastruktura RECETOX (Acronym: RECETOX RI)

Investor: Ministry of Education, Youth and Sports of the CR, RECETOX RI

Files attached

1809778.pdf

Find similar documents

Citovat

STRASSER, Paul, Marina RUSSO, Pauline STADLER, Patrick BREITENEDER, Guenther REDHAMMER, Markus HIMMELSBACH, Oliver BRUGGEMANN, Uwe MONKOWIUS, Petr KLÁN and Ian TEASDALE. Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry. POLYMER CHEMISTRY. Royal Society of Chemistry, 2021, vol. 12, No 47, p. 6927-6936. ISSN 1759-9954. Available from: 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 and Ian TEASDALE. Green-light photocleavable meso-methyl BODIPY building blocks for macromolecular chemistry. \textit{POLYMER CHEMISTRY}. Royal Society of Chemistry, 2021, vol.~12, No~47, p.~6927-6936. ISSN~1759-9954. Available from: https://dx.doi.org/10.1039/d1py01245b.

Detailed Information on Publication Record