Tuning the Solid Phase Fluorescence Emission from Long Wavelength Visible to Near-Infrared in Oxazol-5-One Derivatives: Structure-Property Relationship, Theoretical and Experimental Studies

İbrahim Hanif Nazlı; Gül Yakalı; Derya Topkaya; Merve İzmirli; Sema Demirci Uzun; Serap Alp

doi:10.1007/s10895-023-03158-7

Tuning the Solid Phase Fluorescence Emission from Long Wavelength Visible to Near-Infrared in Oxazol-5-One Derivatives: Structure-Property Relationship, Theoretical and Experimental Studies

J Fluoresc. 2023 Jul;33(4):1481-1494. doi: 10.1007/s10895-023-03158-7. Epub 2023 Feb 10.

Authors

İbrahim Hanif Nazlı^{1

2}, Gül Yakalı³, Derya Topkaya⁴, Merve İzmirli¹, Sema Demirci Uzun⁵, Serap Alp⁴

Affiliations

¹ Department of Chemistry, Graduate School of Natural and Applied Science, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.
² Department of Chemistry, Faculty of Sciences, Izmir Institute of Technology, Urla, 35430, Izmir, Turkey.
³ Department of Engineering Sciences, Faculty of Engineering, Izmir Katip Celebi University, Cigli, 35620, İzmir, Turkey. gul_ozkan13@hotmail.com.
⁴ Department of Chemistry, Faculty of Sciences, Dokuz Eylul University, Buca, 35160, Izmir, Turkey.
⁵ Department of Engineering Sciences, Faculty of Engineering, Izmir Katip Celebi University, Cigli, 35620, İzmir, Turkey.

PMID: 36763296
DOI: 10.1007/s10895-023-03158-7

Abstract

Most of the fluorescent molecules among organic [Formula: see text]-conjugated materials show blue or green emission in the solid phase but few of them emit red-shifted visible and near-infrared light in the material science. To create molecules emitting for this feature, two π-conjugated oxazol-5-one derivatives containing donor (OCH₃) and acceptor groups (NO₂) were synthesized. Their optical and charge-transport properties were investigated through experimental and theoretical methods including the single crystal X-ray crystallography, Hirshfeld Surface Analysis, photophysical studies and Density Functional Theory (DFT), respectively. In addition, FT-IR, ¹H-NMR, ¹³C-NMR spectroscopy, cyclic voltammetry (CV) measurements were performed. According to our results, both molecules may provide the significant pathway of development of long wavelength visible and red emissive features in solid phase with the aggregation induced enhanced emission (AIEE) properties particularly in the fields of OLEDs, optical communication, defence and bioimaging.

Keywords: Aggregation induced enhanced emission (AIEE); Noncovalent interactions; Solid state long wavelength visible and near infrared fluorescence; Stacking interactions.