Modular functional integration of a two-input INH logic gate with a fluorophore-spacer-receptor(1)-spacer-receptor(2) conjugate

• Type: Article in International Scientific Journal
• Date: 2008

Authors

Marek Kluciar (Author) Other; Rita Ferreira (Author) Other; Baltazar de Castro (Author) FCUP; Uwe Pischel (Author) Other

Journal

Title: Journal of Organic Chemistry

Vol. 73

Pages: 6079-6085

ISSN: 0022-3263

Publisher: American Chemical Society

Indexing

ISI Web of Knowledge - 38 Citations

Scopus - 31 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-003-X11

DOI: 10.1021/jo800342t

Abstract (EN): The synthesis and photophysical characterization of a fluorophore-spacer-receptor(1)spacer-receptor(2) system, which combines the 1,8-naphthalimide fluorophore with amine and urea receptor units, is reported. Photoinduced electron transfer (PET) from the amino group was blocked by protonation, leading to a drastic fluorescence enhancement (ca. 20 times). Interaction of the urea receptor with anions (F(-), AcO(-), H(2)PO(4)(-)) via hydrogen bonding or urea NH deprotonation resulted in significant fluorescence quenching of the 1,8-naphthalimide chromophore in an appropriately chosen model compound (ca. 30-45%). In the presence of both chemical input species, protons and anions, the fluorescence was also quenched. The binding of the anions by NH(+) ammonium receptor has been assumed. The apparent anion binding constants of the protonated conjugate follow the basicity trend of the anions: AcO(-) similar to F(-) > H(2)PO(4)(-). The investigated system constitutes an example for the flexible and modular realization of functionally integrated INH logic at the molecular level, using protons and anions as chemical input species and the fluorescence of a PET-active signaling unit as output.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 7