Research output: Contribution to journal › Article › peer-review
Visible‐light Organic Photosensitizers Based on 2‐(2‐Aminophenyl)benzothiazoles for Photocycloaddition Reactions. / Pylova, Ekaterina; Lasorne, Benjamin; McClenaghan, Nathan et al.
In: Chemistry - A European Journal, Vol. 30, No. 68, e202401851, 05.12.2024.Research output: Contribution to journal › Article › peer-review
}
TY - JOUR
T1 - Visible‐light Organic Photosensitizers Based on 2‐(2‐Aminophenyl)benzothiazoles for Photocycloaddition Reactions
AU - Pylova, Ekaterina
AU - Lasorne, Benjamin
AU - McClenaghan, Nathan
AU - Jonusauskas, Gediminas
AU - Taillefer, Marc
AU - Konchenko, Sergey
AU - Prieto, Alexis
AU - Jaroschik, Florian
PY - 2024/12/5
Y1 - 2024/12/5
N2 - We have studied 2-(2-aminophenyl)benzothiazole and related derivatives for their photophysical properties in view of employing them as new and readily tunable organic photocatalysts. Their triplet energies were estimated by DFT calculations to be in the range of 52–57 kcal mol−1, suggesting their suitability for the [2+2] photocycloaddition of unsaturated acyl imidazoles with styrene derivatives. Experimental studies have shown that 2–(2–aminophenyl)benzothiazoles comprising alkylamino groups (NHMe, NHiPr) or the native amino group provide the best photocatalytic results in these visible-light mediated [2+2] reactions without the need of any additives, yielding a range of cyclobutane derivatives. A combined experimental and theoretical approach has provided insights into the underlying triplet-triplet energy transfer process.
AB - We have studied 2-(2-aminophenyl)benzothiazole and related derivatives for their photophysical properties in view of employing them as new and readily tunable organic photocatalysts. Their triplet energies were estimated by DFT calculations to be in the range of 52–57 kcal mol−1, suggesting their suitability for the [2+2] photocycloaddition of unsaturated acyl imidazoles with styrene derivatives. Experimental studies have shown that 2–(2–aminophenyl)benzothiazoles comprising alkylamino groups (NHMe, NHiPr) or the native amino group provide the best photocatalytic results in these visible-light mediated [2+2] reactions without the need of any additives, yielding a range of cyclobutane derivatives. A combined experimental and theoretical approach has provided insights into the underlying triplet-triplet energy transfer process.
UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85208933244&origin=inward&txGid=459618ff8bb93c80c0903dd239d16d64
UR - https://www.mendeley.com/catalogue/571282e7-a984-32db-8089-4a5ac8e83f2b/
U2 - 10.1002/chem.202401851
DO - 10.1002/chem.202401851
M3 - Article
C2 - 39011924
VL - 30
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 68
M1 - e202401851
ER -
ID: 61160472