메뉴 건너뛰기




Volumn 118, Issue 46, 2014, Pages 13279-13289

Preferential molecular encapsulation of an ICT fluorescence probe in the supramolecular cage of cucurbit[7]uril and β-cyclodextrin: An experimental and theoretical approach

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SPECTROSCOPY; CATIONIC SURFACTANTS; CHARGE TRANSFER; COMPLEXATION; CYCLODEXTRINS; DYES; FLUORESCENCE; HYDROPHOBICITY; METAL IONS; PROBES; QUANTUM CHEMISTRY; SPECTROSCOPIC ANALYSIS;

EID: 84912557560     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp5079339     Document Type: Article
Times cited : (24)

References (52)
  • 1
    • 0001805503 scopus 로고
    • Molecular Container Compounds
    • Cram, D. J. Molecular Container Compounds. Nature 1992, 356, 29-36.
    • (1992) Nature , vol.356 , pp. 29-36
    • Cram, D.J.1
  • 4
    • 0001354595 scopus 로고    scopus 로고
    • Industrial Applications of Cyclodextrins
    • Hedges, A. R. Industrial Applications of Cyclodextrins. Chem. Rev. 1998, 98, 2035-2044.
    • (1998) Chem. Rev. , vol.98 , pp. 2035-2044
    • Hedges, A.R.1
  • 5
    • 0032119526 scopus 로고    scopus 로고
    • Cyclodextrin Drug Carrier Systems
    • Uekama, K.; Hirayama, F.; Irie, T. Cyclodextrin Drug Carrier Systems. Chem. Rev. 1998, 98, 2045-2076.
    • (1998) Chem. Rev. , vol.98 , pp. 2045-2076
    • Uekama, K.1    Hirayama, F.2    Irie, T.3
  • 6
    • 0022220842 scopus 로고
    • The Binding of Cyclobutane-1,1-dicarboxylatodiamineplatinum(II) by α-cyclodextrin in Aqueous Solution
    • Alston, D. R.; Lilley, T. H.; Stoddart, J. F. The Binding of Cyclobutane-1,1-dicarboxylatodiamineplatinum(II) by α-cyclodextrin in Aqueous Solution. J. Chem. Soc., Chem. Commun. 1985, 1600-1602.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 1600-1602
    • Alston, D.R.1    Lilley, T.H.2    Stoddart, J.F.3
  • 7
    • 37049093089 scopus 로고
    • The X-ray Crystal Structure of a 1:1 Adduct Between α-cyclodextrin and Cyclobutane-1,1-dicarboxylatodiammineplationum(II)
    • Alston, D. R.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. The X-ray Crystal Structure of a 1:1 Adduct Between α-cyclodextrin and Cyclobutane-1,1-dicarboxylatodiammineplationum(II). J. Chem. Soc., Chem. Commun. 1985, 1602-1604.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 1602-1604
    • Alston, D.R.1    Slawin, A.M.Z.2    Stoddart, J.F.3    Williams, D.J.4
  • 8
    • 77949388516 scopus 로고    scopus 로고
    • "Green" Method for Isolation of Cucurbit[7]uril via a Solid State Metathesis Reaction
    • Jiao, D.; Zhao, N.; Scherman, O. A. A "Green" Method for Isolation of Cucurbit[7]uril via a Solid State Metathesis Reaction. Chem. Commun. 2010, 46, 2007-2009.
    • (2010) Chem. Commun. , vol.46 , pp. 2007-2009
    • Jiao, D.1    Zhao, N.2    Scherman, O.A.A.3
  • 9
    • 0034716334 scopus 로고    scopus 로고
    • New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit-[n]uril (n = 5, 7, and 8)
    • Kim, J.; Jung, I.-S.; Kim, S.-Y.; Lee, E.; Kang, J.-K.; Sakamoto, S.; Yamaguchi, K.; Kim, K. New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit-[n]uril (n = 5, 7, and 8). J. Am. Chem. Soc. 2000, 122, 540-541.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 540-541
    • Kim, J.1    Jung, I.-S.2    Kim, S.-Y.3    Lee, E.4    Kang, J.-K.5    Sakamoto, S.6    Yamaguchi, K.7    Kim, K.8
  • 10
    • 0035977209 scopus 로고    scopus 로고
    • Controlling Factors in the Synthesis of Cucurbituril and its Homologues
    • Day, A.; Arnold, A. P.; Blanch, R. J.; Snushall, B. Controlling Factors in the Synthesis of Cucurbituril and its Homologues. J. Org. Chem. 2001, 66, 8094-8100.
    • (2001) J. Org. Chem. , vol.66 , pp. 8094-8100
    • Day, A.1    Arnold, A.P.2    Blanch, R.J.3    Snushall, B.4
  • 11
    • 84933041004 scopus 로고
    • Condensation Products from Glycoluril and Formaldehyde
    • Behrend, R.; Meyer, E.; Rusche, F. Condensation Products from Glycoluril and Formaldehyde. Liebigs Ann. Chem. 1905, 339, 1-37.
    • (1905) Liebigs Ann. Chem. , vol.339 , pp. 1-37
    • Behrend, R.1    Meyer, E.2    Rusche, F.3
  • 13
    • 0345179962 scopus 로고    scopus 로고
    • The Stability of Cyclodextrin Complexes in Solution
    • Connors, K. A. The Stability of Cyclodextrin Complexes in Solution. Chem. Rev. 1997, 97, 1325-1358.
    • (1997) Chem. Rev. , vol.97 , pp. 1325-1358
    • Connors, K.A.1
  • 14
    • 4243778369 scopus 로고    scopus 로고
    • Complexation Thermodynamics of Cyclodextrins
    • Rekharsky, M. V.; Inoue, Y. Complexation Thermodynamics of Cyclodextrins. Chem. Rev. 1998, 98, 1875-1918.
    • (1998) Chem. Rev. , vol.98 , pp. 1875-1918
    • Rekharsky, M.V.1    Inoue, Y.2
  • 15
    • 0346461917 scopus 로고    scopus 로고
    • Introduction and General Overview of Cyclodextrin Chemistry
    • Szejtli, J. Introduction and General Overview of Cyclodextrin Chemistry. Chem. Rev. 1998, 98, 1743-1754.
    • (1998) Chem. Rev. , vol.98 , pp. 1743-1754
    • Szejtli, J.1
  • 16
    • 0041472445 scopus 로고    scopus 로고
    • Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry
    • Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry. Acc. Chem. Res. 2003, 36, 621-630.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 621-630
    • Lee, J.W.1    Samal, S.2    Selvapalam, N.3    Kim, H.-J.4    Kim, K.5
  • 18
    • 0002492419 scopus 로고
    • Cucurbituril
    • Mock, W. L. Cucurbituril. Top. Curr. Chem. 1995, 175, 1-24.
    • (1995) Top. Curr. Chem. , vol.175 , pp. 1-24
    • Mock, W.L.1
  • 19
    • 18444369800 scopus 로고
    • Cucurbituril: Supramolecular perspective for an old ligand
    • Cintas, P. Cucurbituril: Supramolecular perspective for an old ligand. J. Inclusion Phenom. Mol. Recognit. Chem. 1994, 17, 205-220.
    • (1994) J. Inclusion Phenom. Mol. Recognit. Chem. , vol.17 , pp. 205-220
    • Cintas, P.1
  • 21
    • 34047200582 scopus 로고    scopus 로고
    • Enhancing Fluorescence and Photostability Properties of Dyes
    • Koner, A. L.; Nau, W. M. Enhancing Fluorescence and Photostability Properties of Dyes. Supramol. Chem. 2007, 19, 55-66.
    • (2007) Supramol. Chem. , vol.19 , pp. 55-66
    • Koner, A.L.1    Nau, W.M.2
  • 22
    • 0142072002 scopus 로고    scopus 로고
    • Host Properties of Cucurbit[7]uril: Fluorescence Enhancement of Anilinonaphthalene Sulfonates
    • Wagner, B. D.; Stojanovic, N.; Day, A. I.; Blanch, R. J. Host Properties of Cucurbit[7]uril: Fluorescence Enhancement of Anilinonaphthalene Sulfonates. J. Phys. Chem. B 2003, 107, 10741-10746.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 10741-10746
    • Wagner, B.D.1    Stojanovic, N.2    Day, A.I.3    Blanch, R.J.4
  • 23
    • 25444493939 scopus 로고    scopus 로고
    • Taming Fluorescent Dyes with Cucurbituril
    • Nau, W. M.; Mohanty, J. Taming Fluorescent Dyes with Cucurbituril. Int. J. Photoenergy 2005, 7, 133-141.
    • (2005) Int. J. Photoenergy , vol.7 , pp. 133-141
    • Nau, W.M.1    Mohanty, J.2
  • 24
    • 33846435171 scopus 로고    scopus 로고
    • Supramolecular Dye Laser with Cucurbit[7]uril in Water
    • Mohanty, J.; Pal, H.; Ray, A. K.; Kumar, S.; Nau, W. M. Supramolecular Dye Laser with Cucurbit[7]uril in Water. Chem-PhysChem 2007, 8, 54-56.
    • (2007) Chem-PhysChem , vol.8 , pp. 54-56
    • Mohanty, J.1    Pal, H.2    Ray, A.K.3    Kumar, S.4    Nau, W.M.5
  • 25
    • 20444497394 scopus 로고    scopus 로고
    • Ultrastable Rhodamine with Cucurbituril
    • Mohanty, J.; Nau, W. M. Ultrastable Rhodamine with Cucurbituril. Angew. Chem., Int. Ed. 2005, 44, 3750-3754.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3750-3754
    • Mohanty, J.1    Nau, W.M.2
  • 26
    • 29644438613 scopus 로고    scopus 로고
    • A Green to Blue Fluorescence Switch of Protonated 2-aminoanthracene Upon Inclusion in Cucurbit[7]uril
    • Wang, R.; Yuan, L.; Macartney, D. H. A Green to Blue Fluorescence Switch of Protonated 2-aminoanthracene Upon Inclusion in Cucurbit[7]uril. Chem. Commun. 2005, 5867-5869.
    • (2005) Chem. Commun. , pp. 5867-5869
    • Wang, R.1    Yuan, L.2    Macartney, D.H.3
  • 27
    • 33745431772 scopus 로고    scopus 로고
    • Analysis of Host-Assisted Guest Protonation Exemplified for p- Sulfonatocalix[4]arene - Towards Enzyme-Mimetic pKa Shifts
    • Bakirci, H.; Koner, A. L.; Schwarzlose, T.; Nau, W. M. Analysis of Host-Assisted Guest Protonation Exemplified for p- Sulfonatocalix[4]arene - Towards Enzyme-Mimetic pKa Shifts. Chem. - Eur. J. 2006, 12, 4799-4807.
    • (2006) Chem. - Eur. J. , vol.12 , pp. 4799-4807
    • Bakirci, H.1    Koner, A.L.2    Schwarzlose, T.3    Nau, W.M.4
  • 29
    • 0035801551 scopus 로고    scopus 로고
    • Two Mechanisms of Slow Host - Guest Complexation Between Cucurbit[6]uril and Cyclohexylmethylamine: PH Responsive Supramolecular Kinetics
    • Marquez, C.; Nau, W. M. Two Mechanisms of Slow Host - Guest Complexation Between Cucurbit[6]uril and Cyclohexylmethylamine: pH Responsive Supramolecular Kinetics. Angew. Chem., Int. Ed. 2001, 40, 3155-3160.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3155-3160
    • Marquez, C.1    Nau, W.M.2
  • 30
    • 0029956355 scopus 로고    scopus 로고
    • Molecular Container Assembly Capable of Controlling Bonding and Release of its Guest Molecules: Reversible Encapsulation of Organic Molecules in Sodium Ion Complexed Cucurbituril
    • Jeon, Y. M.; Kim, J.; Whang, D.; Kim, K. Molecular Container Assembly Capable of Controlling Bonding and Release of its Guest Molecules: Reversible Encapsulation of Organic Molecules in Sodium Ion Complexed Cucurbituril. J. Am. Chem. Soc. 1996, 118, 9790-9791.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9790-9791
    • Jeon, Y.M.1    Kim, J.2    Whang, D.3    Kim, K.4
  • 33
    • 1542275582 scopus 로고    scopus 로고
    • Photophysical Properties and Rotational Relaxation Dynamics of Neutral Red Bound b-cyclodextrin
    • Singh, M. K.; Pal, H.; Koti, A. S. R.; Sapre, A. V. Photophysical Properties and Rotational Relaxation Dynamics of Neutral Red Bound b-cyclodextrin. J. Phys. Chem. A 2004, 108, 1465-1474.
    • (2004) J. Phys. Chem. A , vol.108 , pp. 1465-1474
    • Singh, M.K.1    Pal, H.2    Koti, A.S.R.3    Sapre, A.V.4
  • 34
    • 0033536469 scopus 로고    scopus 로고
    • An Exceedingly Long-lived Fluorescent State as a Distinct Structural and Dynamic Probe for Supramolecular Association: An Exploratory Study of Host-guest Complexation by Cyclodextrins
    • Nau, W. M.; Zhang, X. An Exceedingly Long-lived Fluorescent State as a Distinct Structural and Dynamic Probe for Supramolecular Association: An Exploratory Study of Host-guest Complexation by Cyclodextrins. J. Am. Chem. Soc. 1999, 121, 8022-8032.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 8022-8032
    • Nau, W.M.1    Zhang, X.2
  • 35
    • 20444497394 scopus 로고    scopus 로고
    • Ultrastable Rhodamines with Cucurbituril
    • Mohanty, J.; Nau, W. M. Ultrastable Rhodamines with Cucurbituril. Angew. Chem., Int. Ed. 2005, 44, 3750-3754.
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 3750-3754
    • Mohanty, J.1    Nau, W.M.2
  • 36
    • 33645500754 scopus 로고    scopus 로고
    • Host - guest Complexation of Neutral Red with Macrocyclic Host Molecules: Contrasting pKa Shifts and Binding Affinities for Cucurbit[7]uril and b-cyclodextrin
    • Mohanty, J.; Bhasikuttan, A. C.; Nau, W. M.; Pal, H. Host - guest Complexation of Neutral Red with Macrocyclic Host Molecules: Contrasting pKa Shifts and Binding Affinities for Cucurbit[7]uril and b-cyclodextrin. J. Phys. Chem. B 2006, 110, 5132-5138.
    • (2006) J. Phys. Chem. B , vol.110 , pp. 5132-5138
    • Mohanty, J.1    Bhasikuttan, A.C.2    Nau, W.M.3    Pal, H.4
  • 37
    • 18444380577 scopus 로고    scopus 로고
    • A Cucurbit[6]uril Analogue: Host Properties Monitored by Fluorescence Spectroscopy
    • Wagner, B. D.; Boland, P. G.; Lagona, J.; Isaacs, L. A Cucurbit[6]uril Analogue: Host Properties Monitored by Fluorescence Spectroscopy. J. Phys. Chem. B 2005, 109, 7686-7691.
    • (2005) J. Phys. Chem. B , vol.109 , pp. 7686-7691
    • Wagner, B.D.1    Boland, P.G.2    Lagona, J.3    Isaacs, L.4
  • 38
    • 46549089990 scopus 로고    scopus 로고
    • Spectroscopic and Theoretical Evidence for the Photoinduced Twisted Intramolecular Charge Transfer State Formation in N,N-dimethylamino-naphthyl-(acrylo)-nitrile
    • Singh, R. B.; Mahanta, S.; Kar, S.; Guchhait, N. Spectroscopic and Theoretical Evidence for the Photoinduced Twisted Intramolecular Charge Transfer State Formation in N,N-dimethylamino-naphthyl-(acrylo)-nitrile. J. Lumines. 2008, 128, 1421-1430.
    • (2008) J. Lumines. , vol.128 , pp. 1421-1430
    • Singh, R.B.1    Mahanta, S.2    Kar, S.3    Guchhait, N.4
  • 40
    • 0014511643 scopus 로고
    • Quinine Sulfate as a Fluorescence Quantum Yield Standard
    • Fletcher, A. N. Quinine Sulfate as a Fluorescence Quantum Yield Standard. Photochem. Photobiol. 1969, 9, 439-444.
    • (1969) Photochem. Photobiol. , vol.9 , pp. 439-444
    • Fletcher, A.N.1
  • 41
    • 0033515394 scopus 로고    scopus 로고
    • A new ONIOM implementation in Gaussian98. Part I. The Calculation of Energies, Gradients, Vibrational Frequencies and Electric Field Derivatives
    • Dapprich, S.; Komáromi, I.; Byun, K. S.; Morokuma, K.; Frisch, M. J. A new ONIOM implementation in Gaussian98. Part I. The Calculation of Energies, Gradients, Vibrational Frequencies and Electric Field Derivatives. J. Mol. Struct. THEOCHEM 1999, 461-462, 1-21.
    • (1999) J. Mol. Struct. THEOCHEM , vol.461-462 , pp. 1-21
    • Dapprich, S.1    Komáromi, I.2    Byun, K.S.3    Morokuma, K.4    Frisch, M.J.5
  • 42
    • 79953026650 scopus 로고    scopus 로고
    • Studies of Bio-mimetic Medium of Ionic and Non-ionic Micelles by a Simple Charge Transfer Fluorescence Probe N,N-dimethylaminonapthyl-(acrylo)-nitrile
    • Samanta, A.; Paul, B. K.; Guchhait, N. Studies of Bio-mimetic Medium of Ionic and Non-ionic Micelles by a Simple Charge Transfer Fluorescence Probe N,N-dimethylaminonapthyl-(acrylo)-nitrile. Spectrochim. Acta Part A 2011, 78, 1525-1534.
    • (2011) Spectrochim. Acta Part A , vol.78 , pp. 1525-1534
    • Samanta, A.1    Paul, B.K.2    Guchhait, N.3
  • 43
    • 84874000881 scopus 로고    scopus 로고
    • Spectral Modulation of a Charge Transfer Reaction of 2-methoxy-4-(N,N-dimethylamino)-benzaldehyde Inside Cyclodextrin Nanocage
    • Samanta, A.; Jana, S.; Guchhait, N. Spectral Modulation of a Charge Transfer Reaction of 2-methoxy-4-(N,N-dimethylamino)-benzaldehyde Inside Cyclodextrin Nanocage. J. Incl. Phenom. Macrocycl. Chem. 2013, 75, 57-68.
    • (2013) J. Incl. Phenom. Macrocycl. Chem. , vol.75 , pp. 57-68
    • Samanta, A.1    Jana, S.2    Guchhait, N.3
  • 44
    • 4243106516 scopus 로고
    • Environmental and Magnetic Field Effects on Exciplex and Twisted Charge Transfer Emission
    • Bhattacharya, K.; Chowdhury, M. Environmental and Magnetic Field Effects on Exciplex and Twisted Charge Transfer Emission. Chem. Rev. 1993, 93, 507-535.
    • (1993) Chem. Rev. , vol.93 , pp. 507-535
    • Bhattacharya, K.1    Chowdhury, M.2
  • 45
    • 33746190548 scopus 로고
    • A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons
    • Benesi, H. A.; Hildebrand, J. H. A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons. J. Am. Chem. Soc. 1949, 71, 2703-2707.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 2703-2707
    • Benesi, H.A.1    Hildebrand, J.H.2
  • 46
    • 71849103133 scopus 로고    scopus 로고
    • Spectral Modulation of Charge Transfer Fluorescence Probe Encapsulated Inside Aqueous and Non-aqueous β-cyclodextrin Nanocavities
    • Singh, R. B.; Mahanta, S.; Guchhait, N. Spectral Modulation of Charge Transfer Fluorescence Probe Encapsulated Inside Aqueous and Non-aqueous β-cyclodextrin Nanocavities. J. Mol. Struct. 2010, 963, 92-97.
    • (2010) J. Mol. Struct. , vol.963 , pp. 92-97
    • Singh, R.B.1    Mahanta, S.2    Guchhait, N.3
  • 47
    • 45549084946 scopus 로고    scopus 로고
    • Temperature Dependent Simultaneous Ligand Binding in Human Serum Albumin
    • Sinha, S. S.; Mitra, R. K.; Pal, S. K. Temperature Dependent Simultaneous Ligand Binding in Human Serum Albumin. J. Phys. Chem. B 2008, 112, 4884-4891.
    • (2008) J. Phys. Chem. B , vol.112 , pp. 4884-4891
    • Sinha, S.S.1    Mitra, R.K.2    Pal, S.K.3
  • 50
    • 0041472445 scopus 로고    scopus 로고
    • Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry
    • Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Cucurbituril Homologues and Derivatives: New Opportunities in Supramolecular Chemistry. Acc. Chem. Res. 2003, 36, 621-630.
    • (2003) Acc. Chem. Res. , vol.36 , pp. 621-630
    • Lee, J.W.1    Samal, S.2    Selvapalam, N.3    Kim, H.-J.4    Kim, K.5
  • 51
    • 11644249583 scopus 로고
    • Cyclodextrins and Their Applications in Analytical Chemistry
    • Li, S.; Purdy, W. C. Cyclodextrins and Their Applications in Analytical Chemistry. Chem. Rev. 1992, 92, 1457.
    • (1992) Chem. Rev. , vol.92 , pp. 1457
    • Li, S.1    Purdy, W.C.2
  • 52
    • 67049115793 scopus 로고    scopus 로고
    • Control of the Supramolecular Excimer Formation of Thioflavin T within a Cucurbit[8]uril Host: A Fluorescence On/Off Mechanism
    • Mohanty, J.; Dutta Chowdhury, S.; Upadhyaya, H. P.; Bhasikuttan, A. C.; Pal, H. Control of the Supramolecular Excimer Formation of Thioflavin T within a Cucurbit[8]uril Host: A Fluorescence On/Off Mechanism. Chem. - Eur. J. 2009, 15, 5215-5219.
    • (2009) Chem. - Eur. J. , vol.15 , pp. 5215-5219
    • Mohanty, J.1    Dutta Chowdhury, S.2    Upadhyaya, H.P.3    Bhasikuttan, A.C.4    Pal, H.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.