Literature DB >> 27592353

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

Zekeriya Biyiklioglu1, Turgut Keleş2.   

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.

Entities:  

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

Year:  2016        PMID: 27592353     DOI: 10.1007/s10895-016-1921-1

Source DB:  PubMed          Journal:  J Fluoresc        ISSN: 1053-0509            Impact factor:   2.217


  14 in total

Review 1.  Energy, charge, and spin transport in molecules and self-assembled nanostructures inspired by photosynthesis.

Authors:  Michael R Wasielewski
Journal:  J Org Chem       Date:  2006-07-07       Impact factor: 4.354

2.  Signal ratio amplification via modulation of resonance energy transfer: proof of principle in an emission ratiometric Hg(II) sensor.

Authors:  Ali Coskun; Engin U Akkaya
Journal:  J Am Chem Soc       Date:  2006-11-15       Impact factor: 15.419

3.  Cationic polyhedral oligomeric silsesquioxane (POSS) units as carriers for drug delivery processes.

Authors:  Catherine McCusker; Joseph B Carroll; Vincent M Rotello
Journal:  Chem Commun (Camb)       Date:  2005-01-10       Impact factor: 6.222

4.  Development of excellent long-wavelength BODIPY laser dyes with a strategy that combines extending π-conjugation and tuning ICT effect.

Authors:  Dakui Zhang; Virginia Martín; Inmaculada García-Moreno; Angel Costela; M Eugenia Pérez-Ojeda; Yi Xiao
Journal:  Phys Chem Chem Phys       Date:  2011-06-21       Impact factor: 3.676

5.  Synthesis, structure and spectral and electrochemical properties of 3-pyrrolyl BODIPY-metal dipyrrin complexes.

Authors:  V Lakshmi; Way-Zen Lee; M Ravikanth
Journal:  Dalton Trans       Date:  2014-11-14       Impact factor: 4.390

6.  In vitro and in vivo photocytotoxicity of boron dipyrromethene derivatives for photodynamic therapy.

Authors:  Siang Hui Lim; Cliferson Thivierge; Patrycja Nowak-Sliwinska; Junyan Han; Hubert van den Bergh; Georges Wagnières; Kevin Burgess; Hong Boon Lee
Journal:  J Med Chem       Date:  2010-04-08       Impact factor: 7.446

7.  Tetrastyryl-Bodipy dyes: convenient synthesis and characterization of elusive near IR fluorophores.

Authors:  Onur Buyukcakir; O Altan Bozdemir; Safacan Kolemen; Sundus Erbas; Engin U Akkaya
Journal:  Org Lett       Date:  2009-10-15       Impact factor: 6.005

8.  Synthesis, electrochemistry, and electrogenerated chemiluminescence of two BODIPY-appended bipyridine homologues.

Authors:  Honglan Qi; Justin J Teesdale; Rachel C Pupillo; Joel Rosenthal; Allen J Bard
Journal:  J Am Chem Soc       Date:  2013-08-27       Impact factor: 15.419

9.  Characterization of novel fluorescent ligands with high affinity for D1 and D2 dopaminergic receptors.

Authors:  F J Monsma; A C Barton; H C Kang; D L Brassard; R P Haugland; D R Sibley
Journal:  J Neurochem       Date:  1989-05       Impact factor: 5.372

10.  Color tuning in new metal-free organic sensitizers (Bodipys) for dye-sensitized solar cells.

Authors:  Duraisamy Kumaresan; Randolph P Thummel; Thomas Bura; Gilles Ulrich; Raymond Ziessel
Journal:  Chemistry       Date:  2009-06-22       Impact factor: 5.236

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