Vibrational spectra of condensed ring quinones—I 1,4-naphthoquinone and 9,10-anthraquinone

Singh, Shweta; Singh, Rajshree

doi:10.1016/0584-8539(68)80207-7

Cited by 52 publications

(25 citation statements)

References 16 publications

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“…These bands are close to those reported for the ring C À C stretching of 1,4-naphthoquinone and 9,10-anthraquinone in solution (1295, 1328, 1370, 1452 cm À1 ) [47,48] and to the 1333 and 1293 cm À1 ring C À C stretching of anthraquinone-2-carboxylic acid on gold surfaces. [49] The large upward band between 2870 and 3600 cm À1 is assigned to the OÀH stretching of water.…”

supporting

confidence: 83%

“…Bands at similar frequencies were previously reported for the C=O stretch in benzoquinone (BQ) species in solution (1672 cm À1 ), [44] C=O in the oxidized form of thiolated hydroquinone SAMs, that is, H 2 QSH (1647 cm À1 ), [18] H 2 QC 1 SH (1650 cm À1 ) [45] and 2-(11-mercaptoundecyl) hydroquinone (1660 cm À1 ) [14] SAMs are both assigned to the aromatic C=C skeletal stretch of the benzene ring in the anthrahydroquinone form (species appearing). The wavenumbers are close to those reported for an aromatic ring C=C stretching of 1626 [46] and 1580, 1598 cm À1 [47] for anthrahydroquinone derivatives in solution and to the 1580 cm À1 upward band corresponding to the C= C of SAMs formed from 2-(11-mercaptoundecyl) hydroquinone on a gold surface by using in situ IR spectroscopy. [14] The IR spectra for both S-and L-NB SAMs at different surface potentials are presented in Figure S6 (Supporting Information).…”

supporting

confidence: 65%

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Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Darwish

Eggers

Silva

et al. 2011

Chemistry A European J

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Herein, we describe the synthesis of straight (S) and L-shaped (L) norbornylogous bridges (NBs) with an anthraquinone moiety at the distal end as the redox-active head group and two thiol feet at the proximal end, by which the molecules assemble on gold surfaces. The NB molecules were shown to form self-assembled monolayers (SAMs) with a well-behaved surface redox process. The SAMs were characterized by using in situ IR spectroscopy, cyclic voltammetry, scanning tunnelling microscopy and electrochemical impedance spectroscopy. The surface selection rules associated with the IR band intensities allowed the estimation of the position of the anthraquinone moiety with respect to the surface and the tilt of the bridge with respect to the surface normal, both in pure and diluted monolayers. It is shown that the S- and L-NBs hold the plane of the anthraquinone moiety close to the surface normal or the surface tangent, respectively. Neither NB molecule changes its orientation if spaced by diluents on the surface. The difference in the structure of the S- and L-NB SAMs provides a suitable framework for the investigation of factors that govern electron transfer of anthraquinone moieties across self-assembled monolayers with limited structural ambiguity, as compared with the commonly used structurally flexible alkanethiol monolayers.

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supporting

confidence: 83%

supporting

confidence: 65%

Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Darwish

Eggers

Silva

et al. 2011

Chemistry A European J

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“…31,32 The assignments Table 2. Raman wavenumbers (cm 1 ) and assignments of 1,5-DAAQ (band numbering corresponds to the observed band in Fig.…”

Section: Raman Spectral Studiesmentioning

confidence: 99%

“…31,32 In the present compound, the band observed at 3056 cm 1 in both nRs and SERS is assigned to the CH stretching mode (B g . In SERS, the intensity of this band is enhanced and the bandwidth is also increased.…”

Section: Raman Spectral Studiesmentioning

confidence: 99%

“…29 The strong band around 1675 cm 1 in the Raman spectrum of 9,10-anthraquinone is assigned to the C O stretching mode of vibration. 31,32 Generally, the C O band becomes weaker and the wavenumber is lowered on adsorption. 36 The observed bands around 1635 cm 1 in nRs and SERS of the title compound are assigned to the C O stretching vibrational mode (A g ).…”

Section: Raman Spectral Studiesmentioning

confidence: 99%

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Investigations on 1,5‐diaminoanthraquinone by laser excitation

Umadevi

Ramakrishnan

2002

J Raman Spectroscopy

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Optical absorption and fluorescence emission spectra of 1,5-diaminoanthraquinone (1,5-DAAQ) in different solvents and the surface-enhanced Raman scattering (SERS) spectrum of 1,5-DAAQ in silver sol were investigated. Optical absorption and fluorescence emission studies revealed that the internal and external hydrogen bonds and reorientation of the solvent molecule around the excited state fluorophore are responsible for the observed bathochromic shift and the non-radiative decay process in polar solvents. SERS studies showed that 1,5-DAAQ molecules are chemisorbed through carbonyl groups and the lone pair of electrons on the nitrogen. The orientation of the molecule on the silver surface is found to be stand-on.

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Etude de composés d'addition d'acides de Lewis. XXXVI [1] Composés d'addition de l'anthraquinone‐9, 10 et de l'anthrone avec divers acides de Lewis

Giallonardo

Susz

1971

Helvetica Chimica Acta

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Solid stoichiometric adducts of 9, 10‐anthraquinone with SbCl5, ZrCl4, TiCl4 SnCl4, AlCl3, have been prepared. The very important lowering Δω of the IR. carbonyl frequency, ranging from −175 cm−1 for SbCl5 to −117 cm−1 for SnCl4, shows that the acceptor is linked by a dative bond to the carbonyl oxygen atom acting as a donor; an assignment of most of the fundamental IR. frequencies is proposed for anthraquinone and the mentioned adducts. Similar assignments and interpretation have been made for anthrone and its solid adduct with SbCl5, ZrCl4, TiCl4, SnCl4, AlCl3 and ZnCl2, where the CO lowerings range from −164 cm−1 for SbCl5 to −97 cm−1 for ZnCl2.

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Vibrational spectra of condensed ring quinones—I 1,4-naphthoquinone and 9,10-anthraquinone

Cited by 52 publications

References 16 publications

Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Electroactive Self‐Assembled Monolayers of Unique Geometric Structures by Using Rigid Norbornylogous Bridges

Investigations on 1,5‐diaminoanthraquinone by laser excitation

Etude de composés d'addition d'acides de Lewis. XXXVI [1] Composés d'addition de l'anthraquinone‐9, 10 et de l'anthrone avec divers acides de Lewis

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