Citation:
Long Qin, Peng-Fei Duan, Ming-Hua Liu. Interfacial assembly and host-guest interaction of anthracene-conjugated L-glutamate dendron with cyclodextrin at the air/water interface[J]. Chinese Chemical Letters,
;2014, 25(4): 487-490.
doi:
10.1016/j.cclet.2013.12.019
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The interfacial assembly of photo-induced dimerization of atypical anthracene-containing amphiphilic dendron and host-guest interaction with γ-cyclodextrin has been investigated. It has been proved that even without long alkyl chain the amphiphilic dendron could still form stable Langmuir monolayer at the air/water interface. Through the host-guest interaction, γ-cyclodextrin can be used to encapsulate two headgroups of amphiphilic dendron in the antiparallel direction. However, the formed host-guest complex was sensitive to the surface pressure. Slight compression of surface pressure led amphiphilic dendron to reassemble into nanofibers through the strong π-π stacking between headgroups. On the other hand, under in situ irradiation, the amphiphilic dendron was stabilized in the cavity of gcyclodextrin through headgroup dimerization and the host-guest complex further irregularly aggregated to nanoparticles. Meanwhile, γ-cyclodextrin, as a silencer, blocked the supramolecular chirality transfer. Our conclusion was demonstrated through UV/vis, FT-IR, CD spectrum and AFM images, respectively.
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-
-
[1]
[1] D.J. Cram, J.M. Cram, Host-guest chemistry, Science 183 (1974) 803-809.
-
[2]
[2] L.H. Tong, Cyclodextrin Chemistry: Basis and Application, Scientific Press, Beijing, 2001.
-
[3]
[3] M.L. Bender, M. Komiyama, Cyclodextrin Chemistry, Springer-Verlag, Berlin; Heidelberg; New York, 1978.
-
[4]
[4] S. Jozsef, Cyclodextrin Technology, Kluwer Academic Publishers, Dordrecht; Boston; London, 1988.
-
[5]
[5] J. Szijfli, T. Osa, Comprehensive Supramolecular Chemistry: Cyclodextrin, Pergamon, Oxford, UK, 1996.
-
[6]
[6] F. Hapiot, S. Tilloy, E. Monflier, Cyclodextrins as supramolecular hosts for organometallic complexes, Chem. Rev. 106 (2006) 767-781.
-
[7]
[7] G. Wenz, B.H. Han, A. Muller, Cyclodextrin rotaxanes and polyrotaxanes, Chem. Rev. 106 (2006) 782-817.
-
[8]
[8] Y.A. Zhdanov, Y.E. Alekseev, E.V. Kompantseva, Induced optical-activity in cyclodextrin complexes, Russ. Chem. Rev. 61 (1992) 563-575.
-
[9]
[9] A. Ueno, I. Suzuki, T. Osa, Host-guest sensory systems for detecting organic compounds by pyrene excimer fluorescence, Anal. Chem. 62 (1990) 2461-2466.
-
[10]
[10] A. Munoz de la Pena, T. Ndou, J.B. Zung, I.M. Warner, Stoichiometry and formation constants of pyrene inclusion complexes with beta- and gamma-cyclodextrin, J. Phys. Chem. 95 (1991) 3330-3334.
-
[11]
[11] F. Vogtle, W.M. Muller, Complexes of gamma-cyclodextrin with crown ethers, cryptands, coronates and cryptates, Angew. Chem. Int. Ed. 18 (1979) 623-624.
-
[12]
[12] W. Saenger, Cyclodextrin inclusion compounds in research and industry, Angew. Chem. Int. Ed. 19 (1980) 344-362.
-
[13]
[13] F.J. Duan, J.C. Ding, H.J. Deng, et al., An approach to the Paal-Knorr pyrroles synthesis in the presence of b-cyclodextrin in aqueous media, Chin. Chem. Lett. 24 (2013) 706-793.
-
[14]
[14] D.R. Patil, D.S. Dalal, Biomimetic approach for the synthesis of N,N0-diarylsubstituted formamidines catalyzed by b-cyclodextrin in water, Chin. Chem. Lett. 23 (2012) 1125-1128.
-
[15]
[15] A. Nakamura, Y. Inoue, electrostatic manipulate of enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylate with γ-cyclodextrin cavity through chemical modification, J. Am. Chem. Soc. 127 (2005) 5338-5339.
-
[16]
[16] C. Yang, T. Mori, Y. Inoue, et al., Highly stereoselective photocyclodimerization of a-cyclodextrin-appended anthracene mediated by γ-cyclodextrin and cucurbit[ 8]uril: a dramatic steric effect operating outside the binding site, J. Am. Chem. Soc. 130 (2008) 8574-8575.
-
[17]
[17] D.A. Lightner, J.K. Gawronski, K. Gawronska, Conformational enantiomerism in bilirubin. Selection by cyclodextrins, J. Am. Chem. Soc. 107 (1985) 2456-2461.
-
[18]
[18] C. Yang, Recent progress in supramolecular chiral photochemistry, Chin. Chem. Lett. 24 (2013) 437-441.
-
[19]
[19] Y.P. Wang, N. Ma, Z.Q. Wang, X. Zhang, Photocontrolled reversible supramolecular assemblies of an azobenzene-containing surfactant with a-cyclodextrin, Angew. Chem. Int. Ed. 46 (2007) 2823-2826.
-
[20]
[20] Y. Liu, Y.L. Zhao, H.Y. Zhang, Recognition-induced supramolecular porous nanosphere formation from cyclodextrin conjugated by cholic acid, Langmuir 22 (2006) 3434-3438.
-
[21]
[21] R. Kataky, E. Morgan, Potential of enzyme mimics in biomimetic sensors: a modified-cyclodextrin as a dehydrogenase enzyme mimic, Biosens. Bioelectron. 18 (2003) 1407-1417.
-
[22]
[22] K.B. Blodgett, Films built by depositing successive monomolecular layers on a solid surface, J. Am. Chem. Soc. 57 (1935) 1007-1022.
-
[23]
[23] G.G. Roberts, Langmuir-Blodgett Films, Plenum, New York, 1990.
-
[24]
[24] M.C. Petty, Langmuir-Blodgett Films: An Introduction, Cambridge University Press, Cambridge, 1996.
-
[25]
[25] D. Mobius, Molecular cooperation in monolayer organizates, Acc. Chem. Res. 14 (1981) 63-68.
-
[26]
[26] Y.G. Li, M.H. Liu, Induced chirality of supramolecular assemblies of some amphiphiles with b-cyclodextrin through the interaction at the air/water interface, J. Colloid Interface Sci. 306 (2007) 386-390.
-
[27]
[27] P.F. Duan, M.H. Liu, Self-assembly of L-glutamate based aromatic dendrons through the air/water interface: morphology, photodimerization and supramolecular chirality, Phys. Chem. Chem. Phys. 12 (2010) 4383-4389.
-
[28]
[28] P.F. Duan, L. Qin, M.H. Liu, Langmuir-Blodgett films and chiroptical switch of an azobenzene-containing dendron regulated by the in situ host-guest reaction at the air/water interface, Langmuir 27 (2011) 1326-1331.
-
[29]
[29] P.F. Duan, M.H. Liu, Design and self-assembly of L-glutamate-based aromatic dendrons as ambidextrous gelators of water and organic solvents, Langmuir 25 (2009) 8706-8713.
-
[30]
[30] C. Spitz, S. Dähne, A. Ouart, H.W. Abraham, Proof of chirality of J-aggregates spontaneously and enantioselectively generated from achiral dyes, J. Phys. Chem. B 104 (2000) 8664-8669.
-
[31]
[31] H. Bouas-Laurent, A. Castellan, J.P. Desvergne, R. Lapouyade, Photodimerization of anthracenes in fluid solution: structural aspects, Chem. Soc. Rev. 29 (2000) 43-55.
-
[32]
[32] H. Bouas-Laurent, A. Castellan, J.P. Desvergne, Photodimerization of anthracenes in fluid solutions: (part 2) mechanistic aspects of the photocycloaddition and of the photochemical and thermal cleavage, Chem. Soc. Rev. 30 (2001) 248-263.
-
[33]
[33] Q.M. Ji, R. Iwaura, T. Shimizu, Regulation of silica nanotube diameters: sol-gel transcription using solvent-sensitive morphological change of peptidic lipid nanotubes as templates, Chem. Mater. 19 (2007) 1329-1334.
-
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