Abstract
Subsequent treatment of H2TPP(CO2H)4 (tetra(p-carboxylic acid phenyl)porphyrin, 1) with an excess of oxalyl chloride and HNR2 afforded H2TPP(C(O)NR2)4 (R = Me, 2; iPr, 3) with yields exceeding 80%. The porphyrins 2 and 3 could be converted to the corresponding metalloporphyrins MTPP(C(O)NR2)4 (R = Me/iPr for M = Zn (2a, 3a); Cu (2b, 3b); Ni (2c, 3c); Co (2d, 3d)) by the addition of 3 equiv of anhydrous MCl2 (M = Zn, Cu, Ni, Co) to dimethylformamide solutions of 2 and 3 at elevated temperatures. Metalloporphyrins 2a–d and 3a–d were obtained in yields exceeding 60% and have been, as well as 2 and 3, characterized by elemental analysis, electrospray ionization mass spectrometry (ESIMS) and IR and UV–vis spectroscopy. Porphyrins 2, 2a–d and 3, 3a–d are not suitable for organic molecular beam deposition (OMBD), which is attributed to their comparatively low thermal stability as determined by thermogravimetric analysis (TG) of selected representatives.
Highlights
Over the last decades metalloporphyrins have been studied in great detail as they exhibit a high chemical and thermal stability, are aromatic and possess distinctive electrochemical and photophysical properties [1,2,3,4]
Metalloporphyrins 2a–d and 3a–d were obtained in yields exceeding 60% and have been, as well as 2 and 3, characterized by elemental analysis, electrospray ionization mass spectrometry (ESIMS) and IR and UV–vis spectroscopy
Porphyrins 2 and 3 were synthesized as shown in Scheme 1 according to a procedure reported by Gradl et al [18]
Summary
Over the last decades metalloporphyrins have been studied in great detail as they exhibit a high chemical and thermal stability, are aromatic and possess distinctive electrochemical and photophysical properties [1,2,3,4]. Access to the first organic spin valves, which were based on tris(8-hydroxyquinolinato)aluminium (Alq3) sandwiched between La2/3Sr1/3MnO3 and cobalt electrodes, was reported more than a decade ago [5]. This finding motivated the development of Beilstein J. The nature of the molecules integrated into spintronic devices ranges from purely diamagnetic molecules to individual single molecule magnets (SMMs) [4]. Among such molecules metalloporphyrins are very promising in terms of diverse applications [4].
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