Room temperature ionic liquids based on cationic porphyrin derivatives and tetrakis(pentafluorophenyl)borate anion

Abstract

A series of 11 low melting ionic liquids based on meso-substituted A 3 B-porphyrins and A 2 B 2 -porphyrins containing one or two pyridyl substituents have been synthesized in high yields. Three of them are liquids at room temperature. All these porphyrinic salts were characterized by 1 H NMR, 19 F NMR, MALDI-TOF mass spectrometry, elemental analysis and UV-visible spectroscopy. The thermal properties and conductivity values of these salt derivatives have been also measured. A specific conductivity value of up to 4 mS.cm -1 could be obtained for a compound having the counter-anion B(C 6 F 5 ) 4 -.

Non-linear optical, electrochemical and spectroelectrochemical properties of amphiphilic inner salt porphyrinic systems

“…We have reported the synthesis and spectroscopic characterization of new ionic liquid porphyrin derivatives [39]. Starting from the same precursors, we were interested in the design and synthesis of new amphiphilic inner salt porphyrin derivatives.…”

“…The high yield synthesis of ionic porphyrinic systems was recently described using an aldehyde-dipyrromethane condensation in a one-pot reaction [39]. Thus mesosubstituted A 3 B and A 2 B 2 -porphyrins with one or two pyridyl substituents and three or two alkoxy-substituted phenyl groups have been described.…”

“…One of us recently described the preparation and characterization of ionic liquids based on cationic porphyrin derivatives bearing various pyridinium groups at the meso-positions of the macrocycle [39]. In the present paper, we describe the preparation and characterization of these zwitterionic inner salt analogs of such molecules bearing a sulfonato alkylpyridinium group instead of alkylpyridinium with its tetrakis (pentafluorophenyl) borate counterion.…”

Porphyrinic Ionic Liquid Dyes: Synthesis and Characterization

“…combined cationic porphyrin derivative 5‐(4‐ N ‐dodecanoylpyridinium‐4‐yl)‐10,15,20‐tris[3,4,5‐tris(dodecyloxy)‐phenyl]porphyrin with the tetrakis(pentafluorophenyl)borate anion, resulting in porphyrinic ILs . Owing to the high molecular weight and relatively rigid structure of porphyrins, this approach was reported to be limited to porphyrin structures of low symmetry combined with large anions . Zagami et al .…”

“…[11] Incorporation of porphyrin molecules into IL form should also be ag ood strategy to increase the solubility of porphyrins, and thus expand their potentiala pplications.A long these lines, Xu et al combined cationic porphyrin derivative5 -(4-N-dodecanoylpyridinium-4-yl)-10,15,20-tris[3,4,5-tris(dodecyloxy)-phenyl]porphyrin with the tetrakis(pentafluorophenyl)boratea nion,r esulting in porphyrinic ILs. [12] Owing to the high molecular weighta nd relativelyr igid structure of porphyrins, this approach was reported to be limited to porphyrin structures of low symmetry combined with largea nions. [12] Zagami et al [13] tried ad ifferent strategy by combining the anionic meso-tetrakis(4-sulfonatophenyl)porphyrin and cationic trihexyl(tetradecyl)-phosphonium cation, but this approachy ieldedasalt with am elting point of 176.53 8C.In the present work, we chose ad esign strategy that should be applicable to making IL porphryins for ah ost of applications, utilizing highly symmetric porphyrin (D 4h )p recursors (which are easier to synthesize and cheaper in comparison with lower symmetry porphyrins),a dding long alkyl chains (C 12 )i nto their meso positions, [14] and pairingt hem with wellknown IL-forming anions.…”