Photochemical behaviour upon the inclusion for some volatile organic compounds in new fluorescent indolizine β-cyclodextrin sensors

Bécuwe, Matthieu; Lungu, Neculai Catalin; Dron, Paul I.; Fourmentin, Sophie; Landy, David; Surpateanu, Gheorghe

doi:10.1016/j.jphotochem.2006.06.026

Cited by 57 publications

(25 citation statements)

References 38 publications

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“…Due to their unique cup‐like structures, CDs are known to form inclusion complexes in aqueous solution with a large variety of organic targets with a hydrophobic nature and a suitable size and geometry, and are involved in many supramolecular applications 1,2. Because of such an ability to behave as hosts, CDs and their chemically modified derivatives find a wide range of applications that include the areas of drug delivery,2–4 analytical chemistry,5 artificial enzymes,6 photochemical sensors,7 food technology,8 catalysis9 and nanostructured functional materials 10. However, the relatively low values for the binding constants of native CDs or simply modified CD monomers with model substrates appeared to be a limitation in some of their applications.…”

Section: Introductionmentioning

confidence: 99%

β‐Cyclodextrin–Glycerol Dimers: Synthesis and NMR Conformational Analysis

Legros¹,

Vanhaverbeke²,

Souard³

et al. 2013

Eur J Org Chem

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The synthesis of new β‐cyclodextrin dimers linked through their primary faces by different glycerol‐like moieties by click chemistry is described. The unusual behaviour of these cyclodextrin–glycerol dimers in aqueous solution has been studied by NMR spectroscopy. We show that, depending on the length of the linking arm between the two cyclodextrins, the dimers could adopt very different conformations in water: symmetrical or pseudo[1]rotaxane‐like structures through one D‐glucopyranose unit tumbling in one β‐cyclodextrin.

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Section: Introductionmentioning

confidence: 99%

β‐Cyclodextrin–Glycerol Dimers: Synthesis and NMR Conformational Analysis

Legros¹,

Vanhaverbeke²,

Souard³

et al. 2013

Eur J Org Chem

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“…Theoretical studies of indolizines reported so far have been based on semiempirical [9,10], density functional theory (DFT) [6,11], and ab initio [12] methods. Semiempirical [9,10] and DFT [11] calculations have been focusing on the identification of correct reaction mechanisms in syntheses of various indolizine derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…Semiempirical [9,10] and DFT [11] calculations have been focusing on the identification of correct reaction mechanisms in syntheses of various indolizine derivatives. Some theoretical studies [6,12,13] have been concerned with the effects of substituents on several of the various properties of indolizines.…”

Section: Introductionmentioning

confidence: 99%

Effect of substituents on the absorption properties of three pyridylindolizine derivatives: A DFT and TDDFT study

et al. 2009

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“…As a consequence of the structure, the molecule is hydrophilic and features a conical cavity that is essentially hydrophobic in nature. This property enables them to be successfully used as drug carrier, 1-3 separation reagents, 4-6 enzyme mimics, 7,8 photochemical sensors, 9,10 catalysis, 11,12 host-guest interactions, 13 and molecular recognition. 14 In comparison with CD monomers, CD dimers tethered by a spacer of different sizes and shapes have two hydrophobic cavities in a close vicinity.…”

mentioning

confidence: 99%

Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

Hamon¹,

Violeau²,

Turpin³

et al. 2009

Synlett

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The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M -1 using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.Cyclodextrins (CD) are a family of cyclic oligosaccharides composed of a-(1→4)-linked D-glucopyranose units in 4 C 1 chair conformation. The most common CD have six, seven, and eight glucopyranose units and are referred to as a-, b-, and g-CD, respectively. As a consequence of the structure, the molecule is hydrophilic and features a conical cavity that is essentially hydrophobic in nature. This property enables them to be successfully used as drug carrier, 1-3 separation reagents, 4-6 enzyme mimics, 7,8 photochemical sensors, 9,10 catalysis, 11,12 host-guest interactions, 13 and molecular recognition. 14 In comparison with CD monomers, CD dimers tethered by a spacer of different sizes and shapes have two hydrophobic cavities in a close vicinity. 15 This property may afford distinctly different apparent association abilities and molecular selectivities. 16 Various structural architectures of covalent CD dimers could be prepared but one challenge will be to obtain supramolecular CD dimers with noncovalent interactions such as H bonding, staking, electrostatic, and charge-transfer interactions. The equilibrium between the noncovalent dimers and the corresponding monomers could permit to modulate the association. Unexpectedly, these molecular organization behaviors have not been extensively investigated. The supramolecular assembly could be obtained by association of nucleobases such as adenine and thymine or guanine and cytosine. Few examples of CD derivative having nucleobase were described in the literature but only the study of CD monomers were reported. [17][18][19][20][21] In this paper, we reported our preliminary work regarding the synthesis of different CD monomers having a nucleobase such as adenine and thymine and their potential application for the formation of supramolecular CD dimers. The target compounds 8, 9, 11, and 12 had three major structural variations and were novel CD derivatives. First modulation was the glycone moiety: amino-b-CD, azido-b-CD, or amino-permethylated b-CD derivatives. Second variation was the nature of the linker: aminoethyl group or 1,2,3-triazol-4-ylmethyl group. Third modulation was the nucleobase: adenine or thymine.N-Alkylation of pyrimidine bases gave predominantly N1-monosubstituted and N1,N3-bis-substituted derivatives. In order to prepare regioselectively the N1-alkylated pyrimidine, silylation of the nucleobase was developed. Coupling of dibromoethane with silylated thymine (1) in presence of NaI at 105°C without solvent furnished the bromide 2 22-25 in 32% yield. Coupling of propargyl bromide with silylated thymine at 80°C in acetonitrile gave t...

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Photochemical behaviour upon the inclusion for some volatile organic compounds in new fluorescent indolizine β-cyclodextrin sensors

Cited by 57 publications

References 38 publications

β‐Cyclodextrin–Glycerol Dimers: Synthesis and NMR Conformational Analysis

β‐Cyclodextrin–Glycerol Dimers: Synthesis and NMR Conformational Analysis

Effect of substituents on the absorption properties of three pyridylindolizine derivatives: A DFT and TDDFT study

Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs

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