Enhancement of optical properties of new purine nucleobases containing electron-donating and -withdrawing peripheral groups

Author(s)

Zucolotto Cocca, Leandro H. ; Pelosi, Andre G. ; Piguel, Sandrine ; Mendonca, Cleber Renato ; De Boni, Leonardo

• Document type: Journal article
• Source: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY; v. 234, p. 7-pg., 2022-09-01.

Abstract

Nowadays, a great deal of attention has been focused on synthesizing highly fluorescent unnatural base analogs. This has been motivated by the need to overcome the lack of fluorescence of nucleic acids' natural bases. Fluorescent unnatural base analogs, such as purines, may be used in several applications, such as DNA or RNA optical spectroscopy studies. Moreover, for purines base analogs, the optical properties, for example, emission, can be tunable through molecular engineering, improving their applications as fluorescent probes. Looking in this direction, the synthesis and optical spectroscopic studies of a new set of purines base analogs are of foremost relevance. Here, an increase in the fluorescence quantum yield was observed in molecules with NH-pi-CN arrangement. The two-photon absorption (2PA) cross-sections also increased for the lower energy 2PA state. The enhancement of both properties results in a two-photon brightness of 5 and 10 times higher than in compounds lacking the NH-pi-CN arrangement. For the higher energy 2PA state, an excited state absorption contribution to the 2PA cross-section values was observed, that was verified through ultrafast transient absorption measurements. The higher 2PA brightness makes the purines base analogs promising candidates as fluorescent probes in RNA and DNA spectroscopic studies. (AU)

• FAPESP's process: 18/11283-7 - Nonlinear photonics: spectroscopy and advanced processing of materials
• Grantee: Cleber Renato Mendonça
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 16/20886-1 - Ultrafast nonlinear optical spectroscopy: Transient Absorption and optical Kerr Gate with polarization control
• Grantee: Leonardo de Boni
• Support Opportunities: Regular Research Grants
• FAPESP's process: 11/12399-0 - Femtosecond pulses applied to nonlinear optics: spectroscopy, pulse shaping and microfabrication
• Grantee: Cleber Renato Mendonça
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 15/20032-0 - Study on Nonlinear and Charge Transport Properties of Multi-branched Molecules via Quantum Chemical Methods.
• Grantee: Daniel Luiz da Silva
• Support Opportunities: Regular Research Grants