Mono- and 1,1′-Disubstituted Aza Ferrocenyl Compounds: Evidence for an Original Electroactive Fluorescent Species

From Calcium Interaction to Calcium Electrochemical Detection by [(C5H5)Fe(C5H4COCHCHC6H4NEt2)] and Its Two Novel Structurally Characterized Derivatives

“…In the 1 H NMR spectra (CD 3 CN, 400 MHz) the protonation reaction has been confirmed by the appearance of a new signal at δ = 8.64, 9.05, and 8.79 ppm, respectively, attributed to the proton of the NH + group. 1e,25a In molecules 4 and 6 , the NCH 2 -groups appeared at downfield shift position compared with 1 and 3 respectively, as complex multiplets (i.e., δ = 3.69 (dm), 3.62 (dm)), which was consistent with an additive coupling with the acidic proton and the ammonium quaternarization. In the solid state (IR spectrum, KBr), the ν (NH + ) elongation vibrations are located in the 3030−3100 cm -1 expected range of values. 1e,2b,25b Elemental analyses and mass spectra are also in agreement with the proposed formula as described in the Experimental Section.…”

“…The reverse aldol condensation reaction could be suppressed in absence of water. The IR spectra of molecules 1 , 2 , and 3 exhibit vibrations at 1647, 1646, and 1642 cm -1 in CH 3 CN, respectively, assigned to stretching CO vibrations. 9a-c This low value is due to the conjugation of the CO group with the π system (CHCHC 6 H 4 ) in the molecule. 2b,9d These vibrational assignments are presently under theoretical investigation…”

First Fluorescent Ferrocenyl Compound as Multiresponsive Calcium-Sensing Device. NMR, Electrochemical, and Photophysical Preliminary Investigations in CH3CN

“…Compound 1 is a rare example of a molecule containing two different signaling units, for example, redox and fluorescent. As we previously envisaged in our precedent publication,4b we bring now the experimental evidence that it is also a new and original ferrocenyl probe for both the electrochemical and optical detection of Ca(CF 3 SO 3 ) 2 . It was also shown that the whole unsaturated core of the ligand is involved in the binding processes which mainly occur via the CO function and in its vicinity.…”

The First X‐ray Characterized Monosubstituted Ferrocenyl Azacrown Chalcone: Focus on Its Calcium Interaction/Electrochemical Detection Studies

“…The IR spectrum of molecule 2 exhibitsa ν(CO) stretching vibration at 1647 cm –1 in CH 3 CNor in KBr. This low value is due to the conjugation ofthe CO bond with the double bonds of the π‐system(‐CH=CHC 6 H 4 ‐ moiety) in the molecule 2b,10a–10d. We could observe clearly both the characteristic strong stretching vibrations associated with the methylene groups of the crown in the 2873–2941 cm –1 range in CH 3 CN11a and the asymmetrical stretching C–O–C vibrations as a broad band near 1125 cm –1 11b…”

“…We synthesized compound 2 by treatment of acetylferrocene with the appropriate crown aldehyde according to the improved procedure reported for 1a – c 8 (Scheme ). This new procedure allows a significant improvement on the isolated yield of 2 when compared to our original procedure 2b. The product was isolated in good yield (65 %)as a red powder.…”