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Hydroxydialkylamino cruciforms: amphoteric materials with unique photophysical properties

Two amphoteric cruciforms 6 and 7 (XF; 4,4′-[(1E,1′E)-(2,5-bis[4-(dibutylamino)phenyl]ethynyl-1,4-phenylene)bis(ethene-2,1-diyl)]diphenol, 4,4′-[2,5-bis[(E)-4-(dibutylamino)styryl]-1,4-phenylenebis(ethyne-2,1-diyl)]diphenol) were prepared by a Horner reaction followed by a Sonogashira coupling and s...

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Bibliographic Details
Main Authors: McGrier, Psaras (Author) , Solntsev, Kyril M. (Author) , Zucchero, Anthony J. (Author) , Miranda, Oscar R. (Author) , Rotello, Vincent M. (Author) , Tolbert, Laren M. (Author) , Bunz, Uwe H. F. (Author)
Format: Article (Journal)
Language:English
Published: 21 February 2011
In: Chemistry - a European journal
Year: 2011, Volume: 17, Issue: 11, Pages: 3112-3119
ISSN:1521-3765
DOI:10.1002/chem.201002865
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chem.201002865
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201002865
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Author Notes:Psaras L. McGrier, Kyril M. Solntsev, Anthony J. Zucchero, Oscar R. Miranda, Vincent M. Rotello, Laren M. Tolbert, and Uwe H.F. Bunz
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Summary:Two amphoteric cruciforms 6 and 7 (XF; 4,4′-[(1E,1′E)-(2,5-bis[4-(dibutylamino)phenyl]ethynyl-1,4-phenylene)bis(ethene-2,1-diyl)]diphenol, 4,4′-[2,5-bis[(E)-4-(dibutylamino)styryl]-1,4-phenylenebis(ethyne-2,1-diyl)]diphenol) were prepared by a Horner reaction followed by a Sonogashira coupling and subsequent deprotection. The XFs display significant changes in absorption and emission when exposed to trifluoroacetic acid, tetrabutylammonium hydroxide, and metal triflates. The substitution pattern of 6 and 7 leads to spatial separation of the frontier molecular orbitals, which allows the HOMO or LUMO of the XF to be addressed independently by acidic or basic agents. XF 6, which has hydroxyl groups on the styryl axis, displays changes in emission color upon exposure to ten amines in eight different solvents. The change in fluorescence upon the addition of amines was analyzed by linear discriminant analysis. These XFs may have potential in sensor applications for metal cations and amines.
Item Description:Gesehen am 15.08.2022
Physical Description:Online Resource
ISSN:1521-3765
DOI:10.1002/chem.201002865

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