Ferrocenyl chalcones containing anthracenyl group: Synthesis, X-ray crystal structures and electrochemical properties

Electrochemical and Fluorescent Properties of Ferrocenyl Chalcone with N-Ethyl Carbazole Group

“…The extent of the solvatochromic shift of Fc-EtCbz (18 nm) is very close to those of Fc-Anth (16 nm) 7 and Fc-Naph (20 nm), 6 but much less than that of Anth-Fc (44 nm). 7 In spite of the many attempts we made to grow single crystals of Fc-EtCbz using different solvent pairs such as CH 2 Cl 2 /n-hexane, CH 2 Cl 2 /ether and CH2Cl2/MeOH, etc., no single crystals suitable for X-ray structure analysis were obtained. However, based on the above analytical results, we can confirm that the final product is the compound shown in Scheme 1.…”

“…Nevertheless, the pure product was recovered in a yield of less than 20%, which is much lower than those obtained for Fc-Fc (63%), 5 Fc-Naph (73%) 6 and Fc-Anth (57%). 7 In this reaction, the use of stoichiometric amounts of the reactants is important to reduce the amount of side product. For example, the product (Fc-EtCbz) involving the enone moiety can react further with an excess of acetyl reactant to produce the 1,5-pentadione derivative.…”

“…This was also evidenced in other ferrocenyl chalcone systems such as Fc-Fc, 5 Fc-Naph, 6 and Fc-Anth. 7 Moreover, the N-ethyl carbazole group in Fc-EtCbz is more electron donating than the methyl group, if the E 1/2 values of Fc-EtCbz (0.706 V) and ActFc (0.712 V) are compared. Therefore, Fc-EtCbz can be described as a D 1 -π-D 2 system where two different donors (D 1 and D 2 ) are connected through a π-bridge, and the N-ethyl carbazole moiety lowers the HOMO level of Fc-EtCbz, possibly by electron-delocalization over the molecule.…”

“…Recently, we investigated a series of ferrocenyl chalcones linked with aromatic and polycyclic compounds such as ferrocene, 5 naphthalene 6 and anthracene. 7 These systems were designed in order to modulate the electrochemical and optical properties of the polycyclic moieties by the electrondonating ferrocenyl group through the enone linkage. However, the intrinsic optical properties of the naphthalene and anthracene moieties were quenched by the ferrocenyl moiety which acts as a quencher.…”

Electrochemical and Fluorescent Properties of Ferrocenyl Chalcones Containing 1-Naphthalenyl Group: X-ray Crystal Structure of Fc-C(O)CH=CH-(1-Naph)

“…1) shows that the C11=O1 and C12=C13 double bonds of the intervening C11-C12 single bond in the enone moiety are in the s-cis conformation. As for the Fc-PAH compounds where the carbonyl moiety is directly linked to the ferrocenyl group, such as in Fc-2Naph, 9 Fc-9Anth, 11 Fc-EtCbz, 12 and Fcd1Pyr, 14 this type of s-cis conformation is usually observed. In comparison, however, the s-trans conformation is found in the molecular structures of 2Anth-Fc 10 and 9Anth-Fc,…”