ORIGINAL ARTICLE Design, Synthesis, Characterization and Electrochemical Properties of BODIPY Dyes Containing Mono, Bis-2-Naphthyloxyhexyloxy and 4-(Benzyloxy) Phenoxyhexyloxy Groups Zekeriya Biyiklioglu 1 & Turgut Keleş 1 Received: 20 June 2016 /Accepted: 26 August 2016 # Springer Science+Business Media New York 2016 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 di- chloromethane 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. Keywords Synthesis . BODIPY . Electrochemistry . Cyclic voltammetry . 3,4-Dihydroxybenzaldehyde . HOMO-LUMO gap Introduction For over 20 years, 4,4-difluoro-4-bora-3a,4a-diaza-s- indacenes, called boron dipyrromethenes (BODIPYs) have received great attention owing to their outstanding optical properties such as high absorption coefficients, comparatively sharp emission lines, high fluorescence quantum yields, per- fect chemical and photochemical stability and high solubility [1–3]. Boron dipyrromethenes have been used for diverse ap- plications such as chemosensors [4], laser dyes [5, 6], drug delivery [7], electroluminescent films [8], photodynamic therpy of cancer [9, 10], solar cells [11, 12], fluorescent labels [13], optoelectronic devices [14], supramolecular systems [15, 16]. These systems are compatible for synthetic modifications and the electronic properties of BODIPYs which can be fine tuned by introducing appropriate substituents at the BODIPY core [ 17–19]. The first boron difluoride complexes of dipyrromethenes were reported in 1968 [20] and numerous BODIPY syntheses have since been published. Electrochemistry of BODIPY dyes can provide important information about properties of the compounds [21]. Most of research of BODIPY dyes has been concerned with their prop- erties, with fewer publications on their electrochemical prop- erties [22–30]. For these reasons the aim of this study is to synthesize BODIPY dyes containing mono, bis-2- naphthyloxyhexyloxy and 4-(benzyloxy)phenoxyhexyloxy groups and investigate of their electrochemical properties. Experimental The used materials, equipments and the electrochemical mea- surements were supplied as supplementary information. Electronic supplementary material The online version of this article (doi:10.1007/s10895-016-1921-1) contains supplementary material, which is available to authorized users. * Zekeriya Biyiklioglu zekeriya_61@yahoo.com 1 Department of Chemistry, Karadeniz Technical University, 61080 Trabzon, Turkey J Fluoresc DOI 10.1007/s10895-016-1921-1