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Chromophoric and Dendritic Phosphoramidites Enable Construction of Functional Dendrimers with Exceptional Brightness and Water Solubility
Author(s) -
Shaller Andrew D.,
Wan Wei,
Zhao Baoming,
Li Alexander D. Q.
Publication year - 2014
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.201403445
Subject(s) - dendrimer , chromophore , fluorescence , chemistry , solubility , aqueous solution , photochemistry , quantum yield , molecule , combinatorial chemistry , reagent , nanotechnology , materials science , organic chemistry , physics , quantum mechanics
The fluorescence brightness of a molecular probe determines whether it can be effectively measured and its water solubility dictates if it can be applied in real‐world biological systems. However, molecules brighter than the most efficient fluorescent dyes or particles brighter than quantum dots are hard to come by, especially when they must also be soluble in water. In this report, chromophoric phosphoramidites are used in a solid‐state synthesis to construct functional dendrimers. When highly twisted chromophores are chosen and the proper spacers and dendrons are introduced, the resultant dendrimers emit exceptionally bright fluorescence. Chromophores, spacers, and dendrons are stitched together by efficient phosphoramidite reagents, which afford high‐yield water‐soluble phosphodiester linkages after deprotection. The resulting water‐soluble dendrimers are exceptionally bright.