Design, Synthesis, Characterization and Electrochemical Properties of BODIPY Dyes Containing Mono, Bis-2-Naphthyloxyhexyloxy and 4-(Benzyloxy)Phenoxyhexyloxy Groups

Zekeriya Biyiklioglu; Turgut Keleş

doi:10.1007/s10895-016-1921-1

Design, Synthesis, Characterization and Electrochemical Properties of BODIPY Dyes Containing Mono, Bis-2-Naphthyloxyhexyloxy and 4-(Benzyloxy)Phenoxyhexyloxy Groups

J Fluoresc. 2016 Nov;26(6):2257-2266. doi: 10.1007/s10895-016-1921-1. Epub 2016 Sep 3.

Authors

Zekeriya Biyiklioglu¹, Turgut Keleş²

Affiliations

¹ Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Turkey. zekeriya_61@yahoo.com.
² Department of Chemistry, Karadeniz Technical University, 61080, Trabzon, Turkey.

PMID: 27592353
DOI: 10.1007/s10895-016-1921-1

Abstract

In this study, the synthesis of boron dipyrromethene dyes containing mono, bis-2-naphthyloxyhexyloxy and 4-(benzyloxy)phenoxyhexyloxy groups has been reported. Boron dipyrromethene dyes were synthesized from the mono, bis-benzaldehyde derivatives with 2,4-dimethylpyrrole in dichloromethane in the presence of trifluoroacetic, 2,3-dichloro-5,6-dicyano-p-benzoquinon, triethyl amine and boron trifluoride diethyl etherate, respectively. Electrochemical characterization of boron dipyrromethene dyes were carried out with voltammetric measurements. Electrochemical studies show that boron dipyrromethene dyes containing mono, bis-2-naphthyloxyhexyloxy and 4-(benzyloxy)phenoxyhexyloxy groups have reversible one reduction potentials unlike irreversible one oxidation potentials. Graphical Abstract ᅟ.

Keywords: 3,4-Dihydroxybenzaldehyde; BODIPY; Cyclic voltammetry; Electrochemistry; HOMO-LUMO gap; Synthesis.