Fluorescent detection for cyclic and acyclic alcohol guests by naphthalene-appended amino-beta-cyclodextrins.

Spectroscopic and thermodynamic investigations on complexation of naphthalene-appended amino-beta-cyclodextrins 1 and 2 with cyclic alcohols (cyclohexanol and cycloheptanol) and acyclic alcohols (1-pentanol, 2-pentanol, 1-hexanol, and 1-heptanol) have been carried out. Host 1 exhibits a drastic fluorescent enhanced-signal change in the presence of alcohol guests in aqueous solution. [structure: see text]

[1]  A. P. Silva,et al.  Luminescent molecular thermometers , 2006 .

[2]  Yong Chen,et al.  Biquinolino-modified beta-cyclodextrin dimers and their metal complexes as efficient fluorescent sensors for the molecular recognition of steroids. , 2004, Chemistry.

[3]  R. Marchelli,et al.  Enantioselective fluorescence sensing of amino acids by modified cyclodextrins: role of the cavity and sensing mechanism. , 2004, Chemistry.

[4]  Félix Sancenón,et al.  Fluorogenic and chromogenic chemosensors and reagents for anions. , 2003, Chemical reviews.

[5]  Y. Takenaka,et al.  Fluorescent behaviour in host–guest interactions. Part 3. Fluorescent sensing for organic guests using three types of amino-β-cyclodextrins , 2002 .

[6]  H. Nakashima,et al.  Fluorescent behaviour in host–guest interactions. Part 2. Thermal and pH-dependent sensing properties of two geometric isomers of fluorescent amino-β-cyclodextrin derivatives , 2001 .

[7]  F. Hamada,et al.  Synthesis and fluorescent molecular sensing at exciplex emission of pyrene- and cyanobenzene-modified γ-cyclodextrins , 2001 .

[8]  Luca Prodi,et al.  Luminescent chemosensors for transition metal ions , 2000 .

[9]  M. Licchelli,et al.  The design of luminescent sensors for anions and ionisable analytes , 2000 .

[10]  M. Higashi,et al.  Induced circular dichroism spectra of α-, β-, and γ-cyclodextrin complexes with π-conjugate compounds. Part 2. Chiral dimer formation and polarization directions of the π–π* transitions in some hydroxyazo guests having a naphthalene nucleus† , 1999 .

[11]  T. James,et al.  Selective Fluorescence Signalling of Saccharides in Their Furanose Form , 1998 .

[12]  Y. Inoue,et al.  Complexation Thermodynamics of Cyclodextrins. , 1998, Chemical reviews.

[13]  P. Bühlmann,et al.  Carrier-Based Ion-Selective Electrodes and Bulk Optodes. 2. Ionophores for Potentiometric and Optical Sensors. , 1998, Chemical reviews.

[14]  M. Garcia‐Garibay,et al.  Studies of Naphthyl-Substituted β-Cyclodextrins. Self-Aggregation and Inclusion of External Guests , 1998 .

[15]  V. Yam,et al.  Synthesis and optical sensing properties of a boronic acid appended rhenium(I) complex for sugar , 1998 .

[16]  R. Marchelli,et al.  Fluorescent Chemosensor for Organic Guests and Copper(II) Ion Based on Dansyldiethylenetriamine-Modified β-Cyclodextrin , 1997 .

[17]  Masayuki Takeuchi,et al.  FLUORESCENT SENSING OF URONIC ACIDS BASED ON A COOPERATIVE ACTION OF BORONIC ACID AND METAL CHELATE , 1997 .

[18]  M. C. Feiters,et al.  Synthesis of novel dansyl appended cyclodextrins. Self-inclusion and sensor properties , 1997 .

[19]  H. Ikeda,et al.  Fluorescent cyclodextrins for molecule sensing: Fluorescent properties, NMR characterization, and inclusion phenomena of N-dansylleucine-modified cyclodextrins , 1996 .

[20]  Tony D. James,et al.  Fluorescent saccharide receptors: A sweet solution to the design, assembly and evaluation of boronic acid derived PET sensors , 1996 .

[21]  N. Yoshida.  Dynamic aspects in host–guest interactions. Part 4. Kinetic and 1H NMR evidence for multi-step directional binding in the molecular recognition of some 2-naphthylazophenol guests with α-cyclodextrin , 1995 .

[22]  F. Toda,et al.  DANSYL-BETA -CYCLODEXTRINS AS FLUORESCENT SENSORS RESPONSIVE TO ORGANIC COMPOUNDS , 1994 .

[23]  Yoshihisa Inoue,et al.  Calorimetric titration of inclusion complexation with modified .beta.-cyclodextrins. Enthalpy-entropy compensation in host-guest complexation: from ionophore to cyclodextrin and cyclophane , 1993 .

[24]  F. Toda,et al.  Fluorescent Sensors of Molecular Recognition. Modified Cyclodextrins Capable of Exhibiting Guest-Responsive Twisted Intramolecular Charge Transfer Fluorescence , 1993 .

[25]  Yoshihisa Inoue,et al.  Thermodynamics of molecular recognition by cyclodextrins. 1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with .alpha.-, .beta.-, and .gamma.-cyclodextrins: enthalpy-entropy compensation , 1993 .

[26]  T. Osa,et al.  Host-guest sensory systems for detecting organic compounds by pyrene excimer fluorescence , 1990 .

[27]  A. Seiyama,et al.  Dynamic aspects in host-guest interactions: Mechanism for molecular recognition by .alpha.-cyclodextrin of alkyl-substituted hydroxyphenylazo derivatives of sulfanilic acid , 1990 .

[28]  F. Hamada,et al.  Host–Guest Sensory System of Dansyl-Modifled β-Cyclodextrin for Detecting Steroidal Compounds by Dansyl Fluorescence , 1990 .

[29]  T. Osa,et al.  Association dimers, excimers, and inclusion complexes of pyrene-appended .gamma.-cyclodextrins , 1989 .

[30]  Y. Takeda,et al.  Structure elucidation of longikaurin A and longikaurin B, new biologically active diterpenoids from Rabdosia longituba and chemical conversion of oridonin into dihydrolongikaurin A , 1988 .

[31]  N. Yoshida,et al.  Compensation effect in host-guest interactions: the activation parameters for the inclusion reactions of .alpha.-cyclodextrin with hydroxyphenylazo derivatives of naphthalenesulfonic acids , 1987 .

[32]  Y. Matsui,et al.  Binding forces contributing to the association of cyclodextrin with alcohol in an aqueous solution. , 1979 .