Fluorene Analogues of Prodan with Superior Fluorescence Brightness and Solvatochromism
Fluorene Analogues of Prodan with Superior Fluorescence Brightness and Solvatochromism
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DOI：
10.1021/jz9003685
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发表时间：
2010-02-04
影响因子：
5.7
通讯作者：
Klymchenko, Andrey S.
中科院分区：
文献类型：
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作者：
Kucherak, Oleksandr A.;Didier, Pascal;Klymchenko, Andrey S.
为了寻找具有优异性能的环境敏感（溶剂变色）染料，我们通过用芴取代萘核，扩展了最好的溶剂变色染料之一Prodan的电子偶联。新合成的具有强电子给体（二烷基胺）和受体（羰基）基团的芴衍生物在2位和7位表现出红移吸附（接近400 nm），吸收系数（43 000 M-1 cm(-1)）大两倍，双光子吸收截面（类似于400 GM）比Prodan大许多倍。在溶剂中的研究表明，新染料具有更强的荧光溶剂变色性，这与它们的两倍大的过渡偶极矩（14.0 D）有关。与Prodan类似，它们表现出高荧光量子产率，同时它们的光稳定性大大提高。因此，用荧光取代普罗丹中的萘核产生了具有优异光谱和溶剂变色性能的新荧光团。我们期望它们在生物学中找到各种环境敏感探针和标签的应用。
In a search for environment sensitive (solvatochromic) dyes with superior properties, we extended the electronic conjugation of one of the best solvatochromic dyes, Prodan, by substituting its naphthalene core with fluorene. The newly synthesized fluorene derivatives bearing strong electron-donor (dialkylamino) and acceptor (carbonyl) groups the 2 and 7 positions showed red-shited adsorption (close to 400 nm), twice as large of a absorption coefficient (43 000 M-1 cm(-1)) and a manifold larger two photon absorption cross section (similar to 400 GM) compared to Prodan. Studies in solvents revealed much stronger fluoresnce solvatochromism of the new dyes, which is connected with their twice as large transition dipole moment (14.0 D). Similarly to Prodan, they exhibit high fluorescence quantum yields, while their photostability is largely improved. Thus substitution of the naphthalene core in Prodan with fluorence resulted in new fluorophores with superior spectroscopic and solvatochromic properties. We expect them to find a variety of applications as environmentally sensitive probes and labels in biology.