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Hydroxydialkylamino Cruciforms: Amphoteric Materials with Unique Photophysical Properties
Author(s) -
McGrier Psaras L.,
Solntsev Kyril M.,
Zucchero Anthony J.,
Miranda Oscar R.,
Rotello Vincent M.,
Tolbert Laren M.,
Bunz Uwe H. F.
Publication year - 2011
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.201002865
Subject(s) - sonogashira coupling , hydroxide , chemistry , trifluoroacetic acid , homo/lumo , absorption (acoustics) , chromophore , phenylene , photochemistry , polymer chemistry , organic chemistry , molecule , materials science , catalysis , palladium , polymer , composite material
Abstract Two amphoteric cruciforms 6 and 7 (XF; 4,4′‐[(1 E ,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‐phenylene}bis(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.