Is a hydrogen bond responsible for the optical properties of some dihydroxyanthraquinones: Quinizarin and anthraflavic?

Theoretical study of molecular structure and vibrational spectra of 1,4-dihydroxyanthraquinone

“…In the present study, this mode appears at 1648 cm −1 in the Raman spectrum and at 1630 cm −1 in the infrared spectrum as a strong band. According to our calculations, the theoretical frequencies around 1646 and 1638 cm −1 on B3LYP/6-311G++(d,p) level correspond satisfactorily to experimental data, also supported by Bernede et al [39]. It reveals that the related predominant vibration mode mainly be derived from the combination of the C O asymmetric stretching and CC stretching mode, and the C O symmetric stretching and CC stretching vibration mode, respectively.…”

“…But this result is different from those by Smulevich et al [8]. Such effects are commonly observed in associated systems such as carboxylic acid [38] owing to the increased double bond character of the C-O bond on association [39].…”

“…However, we could not observe the strong and sharp bands of O-H vibration in this region of the IR and Raman spectra of 1,4-DAQ since that the OH vibrations are extremely sensitive to the formation of hydrogen bonds, making vibrational spectra more complicated. This phenomenon was also observed by Fabriciova et al [7] and by Bernede et al [39], and explained by the difference in phase state and the hydrogen bonds [7]. Two bands calculated at 3174 and 3172 cm −1 should be assigned to the O-H symmetric and asymmetric stretch relating to intramolecular hydrogen bands.…”

Influence of cetophenolic and diphenolic intramolecular hydrogen bonding on the chromatographic and spectroscopic properties of hydroxyanthraquinones

“…The interpretation of C]O stretching wavenumber value is discussed in specialised literature. This phenomenon would come from the formation of intramolecular hydrogen bonding between oxygen of C]O and hydrogen coming from OH groups at C-1 and C-4 positions [21]. In this case, the presence of two absorption bands for alizarin and only one for the other structures is perfectly justified (Fig.…”

Characterization of alkali halides doped 1-(2-methoxy benzyloxy)-8- hydroxy-9,10-anthraquinone films for photovoltaic applications

“…Different functional derivatives of 9,10-anthraquinone have been synthesised and studied in thin film form [4,5]. The electronic properties of 9,10-anthraquinones are strongly influenced by the nature and the position(s) of the substituent(s).…”