Investigation of the .beta.-cyclodextrin-indole inclusion complex by absorption and fluorescence spectroscopies

Örstan, Aydın; Ross, J. B. Alexander

doi:10.1021/j100295a019

Cited by 121 publications

(57 citation statements)

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“…These two features have been verified for many different compounds and the most promising cases involve drugs and other molecules of biological interest, which have to be analysed in aqueous medium. It is well known that modifications of the electronic properties of the guest start with modifications in its absorption spectrum, as seen for benzene and some of its amino or hydroxy derivatives [65], indole [121] or 1-chloronaphthalene in water or aqueous Dglucose solutions [44]. UV-visible absorption is generally enhanced but at times it may be depressed.…”

Section: Enhancement Of the Fluorescence Of Guests Molecules In Cyclomentioning

confidence: 99%

“…Furthermore, the spectrum is usually bathochromically shifted. Emissions in their turn are enhanced and shifted since excited states and ground state molecules interact differently with the CDs [44,65,121,122]. For analytical work, one should pay attention to the fact that the advantage of a modest enhancement may be offset by the fact that the Stokes shift is often reduced for the complexed versus the free analyte.…”

Section: Enhancement Of the Fluorescence Of Guests Molecules In Cyclomentioning

confidence: 99%

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Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Lerner¹,

Martín²

2000

Analusis

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Introduction Molecular luminescence of analytes in organized media or in supramolecular complexes of cyclodextrinsThe photophysical and photochemical behaviour of molecules complexed to cyclodextrins (CD) is generally different from their behaviour in solution. The first observations in the field were qualitative and were related to the increased stabilisation of labile molecules, mostly drugs, against photodegradation when complexed to natural cyclodextrins [1]. Complexation by CD's was then the preferred subject for those involved in supramolecular chemistry and drug vectorisation techniques [2] as well as in separation techniques [3][4][5]. Stabilization of a molecule against photochemical degradation is still very important in the field of pharmaceutical sciences. A recent example is the stabilisation of promazine as an inclusion complex with β-cyclodextrin [6]. Other photochemists were attracted quite early to this field of research and initiated studies, which were mostly photophysical in nature [7,8]. The key observation was that the formation of supramolecular complexes of analytes with cyclodextrins (CDs) resulted in an increase of their fluorescence quantum yield or even in the appearance of room temperature phosphorescence (RTP) [9][10][11][12]. This enhancement has been used to increase the sensitivity and the selectivity in both luminescence and chromatographic techniques [13-15].We will not say more about RTP with CDs as the subject will be developed in another contribution in the same issue of this Journal. However RTP is also observed in the solubilization of analytes in micellar colloïdal solutions and this field will be reviewed hereunder.These properties have been used to develop analytical techniques, which combine the selectivity of complexation with an enhanced emission [16][17][18][19]. In this way an improvement in the detection limits is obtained in many separation techniques such as HPLC, capillary electrophoresis (CE) or planar chromatography. Furthermore these molecular interactions allow to reveal or to stabilize new molecular forms or to turn species which are normally non-emitting into luminescent ones. All these aspects are reviewed hereunder after a short summary on the nature of the intermolecular interactions, which lie at the heart of these effects. Nature of the interactions between an analyte and a CD or a micelleWithout going into a thorough analysis of the origin of the interactions which exist between molecules in dense media which concern us here, it seems useful to recall the most important factors which should be taken into account when any type of luminescence, fluorescence or phosphorescence is involved.

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Section: Enhancement Of the Fluorescence Of Guests Molecules In Cyclomentioning

confidence: 99%

Section: Enhancement Of the Fluorescence Of Guests Molecules In Cyclomentioning

confidence: 99%

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Lerner¹,

Martín²

2000

Analusis

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“…doi:10.1016/j.jpba.2004.11.008 of the respective inclusion compounds from the influence of the cyclodextrin concentration on their capacity factors. The suitability of the proposed HPLC method for the calculation of the stability constants has been evaluated by comparing the values determined by HPLC with literature data obtained using other methods such as fluorescence spectroscopy and spectrophotometry [11,12,13].…”

Section: Introductionmentioning

confidence: 99%

HPLC and solubility study of the interaction between pindolol and cyclodextrins

Gazpio

Sánchez

García-Zubiri

et al. 2005

Journal of Pharmaceutical and Biomedical Analysis

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“…The driving forces for the complex formation have been attributed to the release of entropy-rich water molecules from the cavity [5], van der Waals interactions [6,7], hydrogen bonding [8 -10], hydrophobic interactions [7,11], release of ring strain in the CD molecule [9], and changes in solvent-surface tension [12].…”

Section: Introductionmentioning

confidence: 99%

Theoretical AM1 studies of inclusion complexes of heptakis(2‐O‐hydroxypropyl)‐β‐cyclodextrins with alkylated phenols

Huang

2004

Int J of Quantum Chemistry

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Semiempirical Austin model I (AM1) calculations have been performed on a family of inclusion complexes of heptakis(2-O-hydroxypropyl)-␤-cyclodextrin isomers derived from the 2-hydroxyl position (2HP␤CD) and from the 6-hydroxyl position (6HP␤CD) with alkylated phenol derivatives. From the stabilization energies and hydrogen bonding studies of the inclusion complexes of 2HP␤CD and 6HP␤CD with substituted phenols in head-first and tail-first positions, we found that the main driving forces for the formation of the inclusion complexes are from the van der Waals interactions.

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Investigation of the .beta.-cyclodextrin-indole inclusion complex by absorption and fluorescence spectroscopies

Cited by 121 publications

References 1 publication

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

HPLC and solubility study of the interaction between pindolol and cyclodextrins

Theoretical AM1 studies of inclusion complexes of heptakis(2‐O‐hydroxypropyl)‐β‐cyclodextrins with alkylated phenols

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