Molecular Nanotube Aggregates of β- and γ-Cyclodextrins Linked by Diphenylhexatrienes

Li, Guang; McGown, Linda B.

doi:10.1126/science.264.5156.249

Cited by 197 publications

(124 citation statements)

References 20 publications

(15 reference statements)

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“…This case of RTP was nicely introduced for PAH and heterocyclic compounds by Scypinsky et al using dibromoethane [9,47,48]. Insoluble infinite string-like sequences with a (1:1) n stoechiometry have been observed for diphenylhexatriene (DPH) [49] and for all-trans retinal [50]. They have been characterized by DSC, NMR, X-ray diffraction and AFM.…”

Section: Different Complexes May Be Obtained For a Given Analytementioning

confidence: 99%

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: Different Complexes May Be Obtained For a Given Analytementioning

confidence: 99%

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

Lerner¹,

Martín²

2000

Analusis

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“…According to the number of the linked glucose units, cyclodextrins can be divided into three classes (α-, β-, and c-cyclodextrin) [21][22][23]. CD is an amphipathic molecule with secondary hydroxyl groups on the wide side and primary hydroxyl groups on the other narrow side.…”

Section: Introductionmentioning

confidence: 99%

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

Cheng

Tian

Huang

et al. 2018

Journal of Chemistry

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e resveratrol functionalized carboxymethyl-β-cyclodextrin conjugate was synthesized by two simple steps. e conjugate was successfully demonstrated by 1 H NMR, 13 C NMR, UV, and FTIR. e photostability of the conjugate was studied by ultraviolet absorption spectrum. After 360 min of UV light irradiation, the conjugate showed a total loss in absorbance of only 12.54%, while the resveratrol and its CM-β-CD inclusion complex showed a total loss in absorbance of 32.15% and 24.05%, respectively. e results indicate that the conjugate was more stable than resveratrol and its CM-β-CD inclusion complex.

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“…There is also an increasing interest in the inclusion of linear molecules inside CDs because of their ability to form composite struc-tures such as molecular nanotube aggregates or polymer chains threaded with CD rings (Li & McGown, 1994;Harada, Li & Kamachi, 1993;Isnin & Kaifer, 1991" Wenz & Keller, 1993 The main features of the ~3-CD host molecule are similar to those of other dimeric 3-CD complexes. The host dimers are formed by O3.--O3 hydrogen bonds between adjacent monomers related by a twofold axis and are packed in channels (see Fig.…”

Section: Commentmentioning

confidence: 99%

β-Cyclodextrin (Z)-9-Dodecen-1-ol 2:1 Complex

Mentzafos¹,

Mavridis²,

Hursthouse³

1996

Acta Crystallogr C

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Molecular Nanotube Aggregates of β- and γ-Cyclodextrins Linked by Diphenylhexatrienes

Cited by 197 publications

References 20 publications

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

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

Resveratrol Functionalized Carboxymethyl-β-Cyclodextrin: Synthesis, Characterization, and Photostability

β-Cyclodextrin (Z)-9-Dodecen-1-ol 2:1 Complex

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