Synthesis and electrochemical characterization of BODIPY dyes bearing polymerizable substituents


BIYIKLIOĞLU Z., KELES T.

INORGANICA CHIMICA ACTA, vol.466, pp.130-138, 2017 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 466
  • Publication Date: 2017
  • Doi Number: 10.1016/j.ica.2017.05.051
  • Journal Name: INORGANICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.130-138
  • Keywords: BODIPY, Synthesis, Morpholin, Electrochemistry, Electropolymerization, PHOTODYNAMIC THERAPY, ELECTROGENERATED CHEMILUMINESCENCE, SPECTROSCOPIC PROPERTIES, ENERGY-TRANSFER, PHOTOSENSITIZERS, DERIVATIVES, BORON, COMPLEXES, DESIGN, PROBE

Abstract

A novel series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes bearing polymerizable 4-morpholin-4-yl-benzyl and 4-(dimethylamino)-1-naphthyl groups were synthesized for the first time and further functionalized in a Knoevenagel condensation reaction with 4-(dimethylamino)-1-naphthaldehyde and 4-morpholin-4-ylbenzaldehyde. The identity of BODIPY dyes 1, 2, 4 were confirmed by H-1 NMR, C-13 NMR, FT-IR, UV-Vis and mass spectrometry. Electrochemical characterizations of boron dipyrromethene dyes were carried out with voltammetric measurements. While the 4-morpholin-4-ylbenzyl and 4-(dimethylamino)-1-naphthyl groups substituted BODIPY dyes 1, 2, 3 and 4 gave common reduction reactions during the cathodic potential scans, BODIPY dyes 1, 2, 3 and 4 were electropolymerized on the working electrode. (C) 2017 Elsevier B.V. All rights reserved.