Synthesis, Molecular Structure, Optical Properties and Electrical Conductivity of Zwitterionic Ferrocenyldithiophosphonates

Abstract

Ferrocenyldithiodiphosphetane [FcPS(μ‐S)]2 [Fc = Fe(η5‐C5H4)(η5‐C5H5)] reacts with the aminoethanol derivatives 1‐ethyl‐3‐pyrrolidinol and 2‐(piperazin‐1‐yl)ethanol to give the zwitterionic (O‐ethylammonium)ferrocenyldithiophosphonates $\rm [FcP(S)S(\overline{C_{4}H_{7}N}HEt)]$ (2) and $\rm [FcP(S)S(OC_{2}H_{4}\overline{NHC_{4}H_{8}N}H)]$ (3), which were fully characterized by elemental analysis, IR and NMR spectroscopy and mass spectrometry. The optical and electrical properties of 2 and 3 as well as those of the previously reported [FcP(S)S(OC2H4NHEt2)] (1) were studied. A molecular structure determination of 1 is also reported.

Triethylammonium (S)-(−)-O-[1-(2-naphthyl)ethyl] (4-methoxyphenyl)dithiophosphonate

“…Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009). Dithiophosphorus compounds and their complexes have been widely investigated in last decades (Heiduc et al, 2006;Karakuş et al, 2007;Gataulina et al, 2008). They have been utilized in agricultural, industrial and medicinal products such as additive to lubricant oils, solvent extraction reagents for metals, floatation agents for minerals, pectidites and insecticides (Thomas et al, 2001;Gray et al, 2003).…”

“…For dithiophosphorus compounds and their complexes, see: Heiduc et al (2006); Karakuş et al (2007); Gataulina et al (2008). For the roles of dithiophosphorus compounds in agricultural, industrial and medicinal products such as additives to lubricant oils, solvent extraction reagents for metals, floatation agents for minerals, pesticides and insecticides, see: Thomas et al (2001); Gray et al (2003).…”

Diastereoselectiveortho-Metalation of a Chiral Ferrocenylphosphonic Diamide and Its Organotin Derivatives

“…Representative examples A–K − for P(V)-containing ferrocene compounds with the P atom directly bound to the ferrocene moiety are shown in Chart . In particular, the P substituents in compounds A and D have proven their ortho-directing effect in lithiation reactions.…”

Ferrocene-Functionalized 4-(2,5-Di(thiophen-2-yl)-1H-pyrrol-1-yl)aniline: A Novel Design in Conducting Polymer-Based Electrochemical Biosensors

“…The resulting yellow-orange crystalline product was filtered and dried under vacuum. 4-(2,5-di(thiophen-2-yl)-1 H -pyrrol-1-yl)amido ferrocenyl dithiophosphonate (SNS-NH 2 -Fc) was obtained in 60% yield [ 26 ].…”