Synthesis of novel dansyl appended cyclodextrins. Self-inclusion and sensor properties

Nelissen, Hubertus F. M.; Venema, Fokke; Uittenbogaard, René M.; Feiters, Martinus C.; Nolte, Roeland J. M.

doi:10.1039/a701142c

Cited by 59 publications

(38 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Protonation of the dansyl moieties: It is known [4] that the amino group of the dansyl chromophoric unit can be quantitatively protonated by trifluoromethylsulfonic (triflic) acid in organic solvents, with strong changes in the absorption and emission spectra. We have found that both reference compound Da and the dansyl moieties of KN(Ao) 2 (Da), KN(Ao)(Da) 2 , and KN(Da) 3 exhibit such spectral changes.…”

Section: Resultsmentioning

confidence: 99%

Amide‐Based Molecular Knots as Platforms for Fluorescent Switches

Passaniti

Ceroni

Balzani

et al. 2006

Chemistry A European J

View full text Add to dashboard Cite

A series of amide-based molecular knots equipped selectively with fluorescent dansyl and/or pyrenesulfonyl moieties were synthesized from the readily available tris(allyloxy)knotane. UV/Vis absorption spectra, emission spectra, and the emission lifetimes of the fluorescent knotanes were investigated in chloroform at 298 K. The absorption spectra of the knotanes correspond to those of mixtures of their UV-active constituents. The fluorescence quantum yields and lifetimes of the dansyl and pyrenesulfonyl moieties are partly quenched by the knotane platform. In the KN(Da)(2)(Py) species, the fluorescent excited state of the dansyl units (lambda(max)=510 nm) lies at lower energy than the fluorescent excited state of the pyrenesulfonyl unit (lambda(max)=385 nm), the emission of which is accordingly quenched with sensitization of the dansyl fluorescence. In the KN(Ao)(2)(Da), KN(Ao)(Da)(2), and KN(Da)(3) species, the addition of acids causes the protonation of their dansyl units with a consequent decrease in the intensity of the dansyl band at 510 nm and appearance of the emission band of the protonated dansyl unit (lambda(max)=340 nm). Each dansyl unit of KN(Ao)(Da)(2) and KN(Da)(3) undergoes the independent protonation. In these incompletely protonated knotanes the fluorescence of the protonated dansyl units is partly quenched by nonprotonated ones. These processes can be quantitatively reversed upon addition of a base. In KN(Da)(2)(Py), an increase of the fluorescence of its pyrenesulfonyl group is observed when the dansyl groups are protonated. The results obtained show that the readily available and easily functionalizable amide-knotanes can be used as an interesting scaffold to obtain fluorescent switches.

show abstract

Section: Resultsmentioning

confidence: 99%

Amide‐Based Molecular Knots as Platforms for Fluorescent Switches

Passaniti

Ceroni

Balzani

et al. 2006

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…We also synthesized the guests: 2-(p-(2'-hydroxyethyl)anilino)-6-naphthalene sulfonate (6) and 2-(p-(3',6',9'-trioxa-11'-hydroxyundecane)anilino)-6-naphthalene sulfonate (7), for which we propose the abbreviations ENS and TENS, respectively .…”

Section: Resultsmentioning

confidence: 99%

“…Monotosylation of triethyleneglycol using NaH as a base gave 34, [7] which was protected with a triphenylmethyl (Trt) group. The protected compound 35 [7] was allowed to react with the alkoxy anion of 2-(4'-aminophenyl)ethyl alcohol to give 36, which was deprotected and treated with 6-amino-2-naphtha- NMR studies: The one-dimensional 13 C and 1 H NMR spectra of compounds 2 and 4 have been described in a preliminary communication. [4] The full assignment of the high-resolution proton spectrum (600 MHz) of 2 was published by us recently.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

et al. 1998

Self Cite

View full text Add to dashboard Cite

The synthesis of homo-and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by aliphatic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked have been transformed into altrose units. The dimers with an octamethylene spacer show self-complexation of the spacer in one of the CD moieties in aqueous solution, as revealed by 1 H and 13 C NMR spectroscopy. Using high-resolution (600 and 800 MHz) NMR spectroscopy and a variety of 2D NMR techniques, an assignment of nearly all of the 1 H NMR signals of two of the CD dimers was made, affording detailed information about the structure of these compounds in water. The self-inclusion of the spacers leads to lower binding affinities for ditopic guest molecules like p-toluidino-6-naphthalene sulfonate (TNS) derivatives and porphyrins. When a rigid 2,2'-bipyridyl group is used to connect the two CD moieties, self-inclusion of the spacer is not possible. This results in the formation of different complexes with ditopic guest molecules, for example, a 2:2 complex with a porphyrin. The CD heterodimers described in this paper contain an a-CD and a b-CD moiety. These dimers display site-specific binding of guest molecules.

show abstract

“…The possibility of using cyclodextrins for sensor purposes, by appending a fluorescent receptor molecule, has been studied by Ueno [6] and others. [7,8] In this type of system, the generation of a signal is based on the competition for the cyclodextrin cavity between the covalently attached fluorophore and an added guest. In the absence of a guest, the fluorophore partially resides inside the cavity.…”

Section: Introductionmentioning

confidence: 99%

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

et al. 2000

View full text Add to dashboard Cite

The dansyl-modified dimer 9 complexes strongly with the steroidal bile salts. Relative to native beta-cyclodextrin, the binding of cholate (1a) and deoxycholate (1b) salts is especially enhanced. These steroids bind exclusively in a 1:1 fashion. For other bile salts (1c-1e) both 1:1 and 1:2 complexes were observed with stabilities similar to those of native beta-cyclodextrin. This indicates that only one cavity is used, with a small contribution from the second. The difference is attributed to the absence of a 12-hydroxy group in the second group of steroids. Comparison with a dimer that lacks the dansyl moiety (6) shows that this group especially hinders the cooperative binding of la and 1b. The smaller interference in the binding of the other steroids indicates that self-inclusion of the dansyl moiety hardly occurs. This weak self-inclusion is supported by fluorescence studies. The dansyl fluorescence of dimer 9 is less blue-shifted than that of other known dansyl-appended cyclodextrin derivatives; this is indicative of a more polar micro-environment. Addition of guests causes a change in fluorescence intensity.

show abstract

Synthesis of novel dansyl appended cyclodextrins. Self-inclusion and sensor properties

Cited by 59 publications

References 21 publications

Amide‐Based Molecular Knots as Platforms for Fluorescent Switches

Amide‐Based Molecular Knots as Platforms for Fluorescent Switches

Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides

Cyclodextrin Dimers as Receptor Molecules for Steroid Sensors

Contact Info

Product

Resources

About