Synthesis and electrochemical characterization of BODIPY dyes bearing polymerizable substituents

BIYIKLIOĞLU Z., KELES T.

INORGANICA CHIMICA ACTA, cilt.466, ss.130-138, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 466
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.ica.2017.05.051
  • Dergi Adı: INORGANICA CHIMICA ACTA
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.130-138
  • Anahtar Kelimeler: BODIPY, Synthesis, Morpholin, Electrochemistry, Electropolymerization, PHOTODYNAMIC THERAPY, ELECTROGENERATED CHEMILUMINESCENCE, SPECTROSCOPIC PROPERTIES, ENERGY-TRANSFER, PHOTOSENSITIZERS, DERIVATIVES, BORON, COMPLEXES, DESIGN, PROBE
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

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.