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Supramolecular Assembly of 2,7‐Dimethyldiazapyrenium and Cucurbit[8]uril: A New Fluorescent Host for Detection of Catechol and Dopamine
Author(s) -
Sindelar Vladimir,
Cejas Mabel A.,
Raymo Françisco M.,
Chen Weizhong,
Parker Samantha E.,
Kaifer Angel E.
Publication year - 2005
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200500917
Subject(s) - catechol , fluorescence , chemistry , supramolecular chemistry , fluorescence spectroscopy , aqueous solution , covalent bond , spectroscopy , ternary operation , host–guest chemistry , proton nmr , analytical chemistry (journal) , crystallography , nuclear chemistry , stereochemistry , molecule , organic chemistry , physics , quantum mechanics , computer science , programming language
The formation of a highly stable inclusion complex between 2,7‐dimethyldiazapyrenium (Me 2 DAP 2+ ) and the cucurbit[8]uril host (CB8) was demonstrated by X‐ray crystallography; MALDI‐TOF mass spectrometry; and 1 H NMR, electronic absorption, and emission spectroscopy. The equilibrium association constant was determined to be 8.9(±0.2)×10 5 L mol −1 from UV‐visible data and 8.4(±1.5)×10 5 L mol −1 from fluorescence data. The Me 2 DAP 2+ ⋅ CB8 inclusion complex acted as a host to bind compounds containing aromatic π‐donor moieties (D), such as catechol and dopamine. This point was demonstrated by 1 H NMR spectroscopy, and electrochemical and emission measurements. Fluorescence detection of the Me 2 DAP 2+ ⋅ D ⋅ CB8 ternary complexes was evident in aqueous solution and on the surface of silica particles, to which fluorescent diazapyrenium units had been covalently immobilized.