%0 Journal Article %1 weissenstein2018watersoluble %A Weißenstein, Annike %A Grande, Vincenzo %A Saha-Möller, Chantu R %A Würthner, Frank %D 2018 %J Org. Chem. Front. %K cells molecular myown organic %P 2641–2651 %R 10.1039/c8qo00611c %T Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines %V 5 %X A large number of water-soluble naphthalene diimides (NDIs) bearing an electron withdrawing chloro and electron-donating amino-substituents with varied electronic character at the core were synthesized by a two-step synthetic approach comprising imidization of 2,6-dichloronaphthalene dianhydride with L-glutamic acid or 2-dimethylaminoethylamine and subsequent nucleophilic substitution of a chlorine atom with primary amines. These new donor–acceptor NDI dyes show absorption and emission maxima beyond 500 nm and fluorescence quantum yields up to 39% in aqueous phosphate buffer solution at acidic and neutral pH values. Our studies revealed a significant effect of core amino-substituents on the optical properties of these NDIs. With increasing electron-withdrawing character of the residues of amino-substituents the absorption and emission maxima are more hypsochromically shifted and the fluorescence quantum yields are markedly increased with the highest value of 39% for NDIs containing a strongly electron withdrawing trifluroethyl group in the amino-substituent. Furthermore, the high reactivity of the core-dichlorinated NDI dye could be utilized for the optical detection of primary amines and biogenic diamines putrescine and cadaverine.

@article{weissenstein2018watersoluble, abstract = {A large number of water-soluble naphthalene diimides (NDIs) bearing an electron withdrawing chloro and electron-donating amino-substituents with varied electronic character at the core were synthesized by a two-step synthetic approach comprising imidization of 2,6-dichloronaphthalene dianhydride with L-glutamic acid or 2-dimethylaminoethylamine and subsequent nucleophilic substitution of a chlorine atom with primary amines. These new donor–acceptor NDI dyes show absorption and emission maxima beyond 500 nm and fluorescence quantum yields up to 39% in aqueous phosphate buffer solution at acidic and neutral pH values. Our studies revealed a significant effect of core amino-substituents on the optical properties of these NDIs. With increasing electron-withdrawing character of the residues of amino-substituents the absorption and emission maxima are more hypsochromically shifted and the fluorescence quantum yields are markedly increased with the highest value of 39% for NDIs containing a strongly electron withdrawing trifluroethyl group in the amino-substituent. Furthermore, the high reactivity of the core-dichlorinated NDI dye could be utilized for the optical detection of primary amines and biogenic diamines putrescine and cadaverine.}, added-at = {2018-09-14T15:22:38.000+0200}, author = {Weißenstein, Annike and Grande, Vincenzo and Saha-Möller, Chantu R and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/26ea8f60fb50f0c6f114dff858f3b1b22/wuerthner_group}, doi = {10.1039/c8qo00611c}, interhash = {e7e417b7b73c79b0184da5940aaaf0c3}, intrahash = {6ea8f60fb50f0c6f114dff858f3b1b22}, journal = {Org. Chem. Front.}, keywords = {cells molecular myown organic}, month = {September}, pages = {2641–2651}, timestamp = {2020-06-29T14:27:20.000+0200}, title = {Water-soluble naphthalene diimides: synthesis, optical properties, and colorimetric detection of biogenic amines}, volume = 5, year = 2018 }