A green to blue fluorescence switch of protonated 2-aminoanthracene upon inclusion in cucurbit[7]uril.

The inclusion of protonated 2-aminoanthracene in the cavity of cucurbit[7]uril increases its pKa values in the ground and excited states, resulting in the disappearance of the green emission of the neutral excited state and the significant enhancement of the blue emissions from the protonated excited state guest.

[1]  Z. Grabowski,et al.  Excited states of aminoanthracenes. An experimental approach to electron density distribution , 1969 .

[2]  Tomas C. Bellamy,et al.  On the activation of soluble guanylyl cyclase by nitric oxide , 2001, Proceedings of the National Academy of Sciences of the United States of America.

[3]  S. Schulman,et al.  Electronic spectra and electronic structures of aminoanthracenes. , 1973, Journal of pharmaceutical sciences.

[4]  Kimoon Kim.  Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. , 2002, Chemical Society reviews.

[5]  A. Kaifer,et al.  Modes of binding interaction between viologen guests and the cucurbit[7]uril host. , 2004, Organic Letters.

[6]  B. Wagner,et al.  Host Properties of Cucurbit(7)uril: Fluorescence Enhancement of Anilinonaphthalene Sulfonates , 2003 .

[7]  W. Nau,et al.  Two Mechanisms of Slow Host-Guest Complexation between Cucurbit[6]uril and Cyclohexylmethylamine: pH-Responsive Supramolecular Kinetics. , 2001, Angewandte Chemie.

[8]  B. Wagner,et al.  A fluorescent host-guest complex of cucurbituril in solution: a molecular Jack O'Lantern , 2001 .

[9]  W. Nau,et al.  Polarizabilities Inside Molecular Containers This work was supported by the Swiss National Science Foundation (projects 620-58000.99 and 4047-057552) within the program NFP 47 "Supramolecular Functional Materials". , 2001, Angewandte Chemie.

[10]  L. Arnaut,et al.  Excited-state proton transfer reactions I. Fundamentals and intermolecular reactions , 1993 .

[11]  B. Wagner,et al.  Fluorescence Enhancement of Curcumin upon Inclusion into Cucurbituril , 2004 .

[12]  Eunsung Lee,et al.  New Cucurbituril Homologues: Syntheses, Isolation, Characterization, and X-ray Crystal Structures of Cucurbit[n]uril (n = 5, 7, and 8) , 2000 .

[13]  Y. Ko,et al.  Unprecedented host-induced intramolecular charge-transfer complex formation. , 2002, Chemical communications.

[14]  A. Kaifer,et al.  Molecular encapsulation by cucurbit[7]uril of the apical 4,4'-bipyridinium residue in newkome-type dendrimers. , 2003, Angewandte Chemie.

[15]  A. Kaifer,et al.  Binding selectivity of cucurbit[7]uril: bis(pyridinium)-1,4-xylylene versus 4,4'-bipyridinium guest sites. , 2004, Organic letters.

[16]  M. Kuz’min,et al.  RUSSIAN CHEMICAL REVIEWS , 2005 .

[17]  Barry B Snushall,et al.  Controlling factors in the synthesis of cucurbituril and its homologues. , 2001, The Journal of organic chemistry.

[18]  F. Raymo,et al.  Tight inclusion complexation of 2,7-dimethyldiazapyrenium in cucurbit[7]uril , 2005 .

[19]  G. Porter,et al.  Acidity constants of anthracene derivatives in singlet and triplet excited states , 1968 .

[20]  A. Kaifer,et al.  Cucurbit[7]uril: a very effective host for viologens and their cation radicals. , 2002, Organic letters.

[21]  Y. Ko,et al.  A stable cis-stilbene derivative encapsulated in cucurbit[7]uril. , 2003, Chemical communications.

[22]  A. Kaifer,et al.  Unusual Electrochemical Properties of the Inclusion Complexes of Ferrocenium and Cobaltocenium with Cucurbit[7]uril , 2003 .

[23]  Jae Wook Lee,et al.  Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. , 2003, Accounts of chemical research.

[24]  B. Wagner,et al.  Cyclodextrin-, UV-, and high pH-induced fluorescence enhancement of the pesticide azinphos-methyl: Applications to its trace analysis , 2002 .

[25]  D. Macartney,et al.  α- and β-Cyclodextrin Rotaxanes of μ-Bis(4-pyridyl)bis[pentacyanoferrate(II)] Complexes , 2000 .

[26]  A. Kaifer,et al.  Complexation of ferrocene derivatives by the cucurbit[7]uril host: a comparative study of the cucurbituril and cyclodextrin host families. , 2005, Journal of the American Chemical Society.

[27]  H. Shizuka,et al.  Proton-transfer reactions in the excited state of phenanthrylamines by nanosecond spectroscopy and fluorimetry , 1982 .