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Generation of the Thymine Triplet State by Through‐Bond Energy Transfer
Author(s) -
Miro Paula,
GomezMendoza Miguel,
Sastre Germán,
Cuquerella M. Consuelo,
Miranda Miguel A.,
Marin M. Luisa
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900830
Subject(s) - benzophenone , thymine , cholic acid , chemistry , triplet state , photochemistry , chromophore , photosensitizer , deoxycholic acid , covalent bond , lithocholic acid , dna , molecule , organic chemistry , bile acid , biochemistry
Benzophenone (BP) and drugs containing the BP chromophore, such as the non‐steroidal anti‐inflammatory drug ketoprofen, have been widely reported as DNA photosensitizers through triplet–triplet energy transfer (TTET). In the present work, a direct spectroscopic fingerprint for the formation of the thymine triplet ( 3 Thy*) by through‐bond (TB) TTET from 3 BP* has been uncovered. This has been achieved in two new systems that have been designed and synthesized with one BP and one thymine (Thy) covalently linked to the two ends of the rigid skeleton of the natural bile acids cholic and lithocholic acid. The results shown here prove that it is possible to achieve triplet energy transfer to a Thy unit even when the photosensitizer is at a long (nonbonding) distance.