Photophysical properties of 3-arylthioimidazo[1,2-a]pyridine derivatives: The role of peripheral electron-donating and electron-withdrawing groups in the advance of organic materials engineering

Abstract

3-Arylthioimidazo[1,2-a]pyridine derivatives may present potential use in fields such as optoelectronics, organic light-emitting diodes (OLEDs), bioimaging, and may be employed as bioprobes in DNA and RNA. However, before these materials can be used for such applications, it is necessary to assess their photophysical properties. Here, we investigated the photophysical properties of five novel 3-arylthioimidazo[1,2-a]pyridine derivatives with different peripheral electron-withdrawing and electron-donating groups. The use of spectroscopic techniques, including UV–vis absorption, fluorescence, time-resolved fluorescence spectroscopy, combined with quantum chemical calculations, allowed us to gain a comprehensive understanding of the compounds' photophysical properties. The results revealed that the 3-arylthioimidazo[1,2-a]pyridine derivatives possess remarkable emissive properties, with a 4.5-fold increase when substituting the trifluoromethyl group for a methoxy group. Furthermore, it has been observed that the compounds containing peripheral groups with halogen atoms exhibit fluorescence quenching. The electron-withdrawing character of the imidazo[1,2-a]pyridine and the position of the lateral substituent hindered the impact of electron-withdrawing groups, while electron-donating groups enhanced the photophysical properties, resulting in increased Stokes shift, larger permanent dipole moment difference, and charge displacement. In conclusion, this study provides key insights into the photophysics of 3-arylthioimidazo[1,2-a]pyridine derivatives and the role of peripheral electron-donating and electron-withdrawing groups. These findings hold great potential for the advancement of optical materials and set foundation for future technological applications.