Generation of the Thymine Triplet State by Through‐Bond Energy Transfer. Issue 28 (26th April 2019)

• Record Type: Journal Article
• Authors: Miro, Paula; Gomez‐Mendoza, Miguel; Sastre, Germán; Cuquerella, M. Consuelo; Miranda, Miguel A.; Marin, M. Luisa
• Is Part Of: Chemistry. Volume 25:Issue 28(2019)
• Page Start: 7004
• Page End: 7011
• Publication Date: 2019-04-26
• Subjects: DNA damage -- energy transfer -- laser flash photolysis -- photochemistry -- steroids; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201900830
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: 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. Abstract : Thymine triplet state . Spectroscopic evidence supporting the formation of the thymine triplet ( 3 Thy*) upon benzophenone (BP) photosensitization has been uncovered in two new systems in which BP and Thy are covalently linked to the two ends of the rigid skeleton of the natural bile acids cholic and lithocholic acid at a nonbonding distance. Thus, 3 Thy* is generated by through‐bond triplet–triplet energy transfer (TTET) from 3 BP* (see figure).