Jump to main content
Jump to site search

Issue 25, 2019

Tracking the origin of photostability in purine nucleobases: the photophysics of 2-oxopurine

Author affiliations

Abstract

This work scrutinizes the relaxation mechanism of 2-oxopurine. Contrary to its ancestor, purine, which is a UVC chromophore, 2-oxopurine shows a red-shifted absorption spectrum centered in the UVA region. In 2-oxopurine, relaxation along the ππ* spectroscopic state directs the population from the Franck–Condon (FC) region towards a minimum, which acts as a crossroad for the further decay of the system either to triplet states or, alternatively, to the ground state through a C6-puckered S1/S0 funnel. A comparison of the optical properties and excited state potential energy surfaces of purine, 2-oxopurine, 2-aminopurine, 6-oxopurine and adenine, allows establishing how the position and nature of substituent tune the photophysics of purine. For this series, we conclude that both C2 and C6 substitution redshift the absorption spectrum of purine, with 2-oxo substitution exhibiting the largest shift. An important exception is the canonical nucleobase adenine, which presents a blue shifted absorption spectrum. The topography of purine's ππ* potential energy surface experiences major changes when functionalized at the C6 position. In particular, the disappearance of the minimum along the ππ* potential energy surface efficiently funnels the excited state population from the FC region to the ground state and increases the photostability of 6-aminopurine (adenine) and 6-oxopurine (hypoxanthine) nucleobases.

Graphical abstract: Tracking the origin of photostability in purine nucleobases: the photophysics of 2-oxopurine

Supplementary files

Article information


Submitted
13 Feb 2019
Accepted
01 Jun 2019
First published
04 Jun 2019

Phys. Chem. Chem. Phys., 2019,21, 13467-13473
Article type
Paper
Author version available

Tracking the origin of photostability in purine nucleobases: the photophysics of 2-oxopurine

L. Martínez-Fernández, S. Arslancan, D. Ivashchenko, C. E. Crespo-Hernández and I. Corral, Phys. Chem. Chem. Phys., 2019, 21, 13467 DOI: 10.1039/C9CP00879A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements