Synthesis and spectral properties of symmetrically arylated BODIPY dyes: Experimental and computational approach

• Published in: Journal of molecular structure 2023-11, Vol.1291, p.135962, Article 135962
• Main Authors: Yilmaz, Raşit Fikret, Derin, Yavuz, Misir, Büşra Albayrak, Atalay, Vildan Enisoğlu, Tutar, Ömer Faruk, Ökten, Salih, Tutar, Ahmet
• Format: Article
• Language: English
• Subjects: Arylated BODIPY; BODIPY; DFT study; Photophysical properties; Spectral shifts; Suzuki coupling
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135962

•Effective synthesis of arylated BODIPY dyes via bromination and Suzuki Coupling.•The electron density of π-conjugated groups at different positions led to blue or red shifted spectra.•The electron accepting at meso and donating groups at C3/C5 of dyes lead red shifted spectra.•The electron donating at meso and accepting groups at C3/C5 of dyes lead blue shifted spectra.•The lowest HOMO-LUMO band gap by binding -SCH3 at C-3/C-5 of BODIPY. In this study, a series of symmetrically arylated BODIPY dyes were synthesized using a pre-functionalization method, and their structures were characterized by several spectroscopic methods. The relationship between the aryl substitution pattern and the photophysical and electrochemical properties of the dyes was investigated using experimental and computational methods. It was found that electron-donating π-conjugated groups at the meso position and electron-accepting π-conjugated groups at the C3/C5 position led to blue-shifted spectra, while the opposite substitution pattern resulted in red-shifted spectra. Additionally, inductive electron-donating alkyl groups at the meso position produced a blue spectral shift and an alkyl group at the meso position significantly increased the fluorescence quantum yield compared to the arylated counterparts. Computational investigations revealed that a thioanisyl group at the C3/C5 position resulted in a significantly narrow band gap. These results provide valuable insights into the design and development of new BODIPY dyes with tailored properties for various applications. [Display omitted]