Charge transfer complexes involving calix[4]resorcinarenes: potential candidates for non-linear optics

Pietraszkiewicz, Oksana; Koźbiał, Małgorzata; Pietraszkiewicz, Marek

doi:10.1002/(sici)1099-0712(1998090)8:5<277::aid-amo356>3.0.co;2-s

Cited by 8 publications

(3 citation statements)

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“…Besides their use as synthetic host compounds,5 resorcarenes have been used as surfactants for encapsulating neutral gold nanoclusters6 and as interior units in dendritic photo‐resistant material 7. Lipophilic resorcarenes can form charge‐transfer molecular complexes which have been of interest for their potential electronic, non‐linear optical, semiconducting and photoconducting properties 8…”

Section: Methodsmentioning

confidence: 99%

Mass spectrometric studies of benzoxazine resorcarenes

Hakala

Nuutinen

Straub

et al. 2002

Rapid Comm Mass Spectrometry

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Eleven differently substituted 3,4-dihydro-2H-1,3-benzoxazine resorcarenes were studied by electrospray ionisation (ESI) and matrix-assisted laser desorption/ionisation (MALDI) mass spectrometry, using Fourier transform ion cyclotron resonance (FT-ICR) and time-of-flight (TOF) mass spectrometers, respectively. Under ESI conditions it was possible to transfer the intact resorcarenes from solution to the gas phase, yielding [M + H](+) and [M + 2H](+) ions as the main ions observed. Energy increase of the ions induced ready decomposition through successive eliminations of four CH(2)NR groups. Ion-molecule reactions showed that the ionising proton was situated somewhere inside the molecule and could not be reached with neutral reagent gases. In the host-guest complexation experiments, the benzoxazine resorcarenes studied turned out to be poor hosts for alkali metal and ammonium ions. In MALDI experiments, 2,5-dihydroxybenzoic acid proved to be the best matrix for these compounds. However, the intensity of the [M + H](+) ions was low for all compounds, and extensive fragmentation with consecutive elimination of CH(2)NR groups was observed.

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Section: Methodsmentioning

confidence: 99%

Mass spectrometric studies of benzoxazine resorcarenes

Hakala

Nuutinen

Straub

et al. 2002

Rapid Comm Mass Spectrometry

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“…Such a cooperative involvement of the host and the guest in delocalizing the electron cloud could be the cause for the charge‐transfer transition, as was observed from UV/Vis spectroscopy. Participation of resorcin[4]arene and gatifloxacin individually in charge‐transfer process with electron‐deficient species is known . However, the present case represents a less known phenomenon, which involves an interplay between hydrogen bond and charge‐transfer interaction .…”

Section: Discussionmentioning

confidence: 86%

Multifaceted Supramolecular Interactions from C‐Methylresorcin[4]arene Lead to an Enhancement in In Vitro Antibacterial Activity of Gatifloxacin

Dawn

Chandra

Ade-Browne

et al. 2017

Chemistry A European J

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Mimicking the antibacterial activity of polyphenols in synthetic systems is an attractive approach for the development of new active pharmaceutical ingredients. Resorcinarenes represent a class of polyphenols, which have been exploited for decades for their attractive chemical scaffold suitable for forming host-guest complexes with hydrophobic guest molecules. However, the polyphenolic character of resorcinarenes, which could be a potential asset to the pharmaceutical industry, have been least exploited. The present work represents an unprecedented interplay of antimicrobial activity of resorcinarene together with its ability to interact chemically with an antibacterial drug gatifloxacin, improving the overall antibacterial activity. The chemistry and the clinical activities involved in this study were investigated simultaneously by spectroscopic techniques, as well as by in vitro measurement of antibacterial activity toward two human bacterial pathogens, a Gram-positive pathogen Staphylococcus aureus and a Gram-negative lung pathogen Legionella pneumophila. The initial positive result obtained from this study could revolutionize the use of synthetically modifiable resorcinarenes and their analogues in fine tuning the clinical behavior of drugs.

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“…28,29 There are reports on the second harmonic generation of calix [4]resorcinarene, 30 the NLO polarization of calix[n]arene with different geometry, 31 all-optical photorefractive properties, and charge transfer complexes of calix [4]resorcinarene-based derivatives. 32,33 The literature rarely reports the third-order optical nonlinearity of calix [4]resorcinarene-derived molecules, even though their guest-host nature and capacity to entrap nanoparticles are reported in the literature. [34][35][36] The enhanced third-order nonlinearity of noncovalently functionalized calix [4]resorcinarene with graphene oxide/silver nanoparticles is reported in the literature.…”

Section: Introductionmentioning

confidence: 99%