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Molecular Logic Gates and Switches Based on 1,3,4‐Oxadiazoles Triggered by Metal Ions
Author(s) -
Li AiFang,
Ruan YiBin,
Jiang QianQian,
He WenBin,
Jiang YunBao
Publication year - 2010
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.200903265
Subject(s) - substituent , oxadiazole , metal ions in aqueous solution , fluorescence , metal , chelation , denticity , chemistry , molecule , ion , pyridine , atom (system on chip) , materials science , inorganic chemistry , stereochemistry , computer science , medicinal chemistry , organic chemistry , physics , embedded system , quantum mechanics
Organic molecular devices for information processing applications are highly useful building blocks for constructing molecular‐level machines. The development of “intelligent” molecules capable of performing logic operations would enable molecular‐level devices and machines to be created. We designed a series of 2,5‐diaryl‐1,3,4‐oxadiazoles bearing a 2‐( para ‐substituted)phenyl and a 5‐( o ‐pyridyl) group (substituent X=NMe 2 , OEt, Me, H, and Cl; 1 a – e ) that form a bidentate chelating environment for metal ions. These compounds showed fluorescence response profiles varying in both emission intensity and wavelength toward the tested metal ions Ni 2+ , Cu 2+ , Zn 2+ , Cd 2+ , Hg 2+ , and Pb 2+ and the responses were dependent on the substituent X, with those of 1 d being the most substantial. The 1,3,4‐oxadiazole O or N atom and pyridine N atom were identified as metal‐chelating sites. The fluorescence responses of 1 d upon metal chelation were employed for developing truth tables for OR, NOR, INHIBIT, and EnNOR logic gates as well as “ON‐OFF‐ON” and “OFF‐ON‐OFF” fluorescent switches in a single 1,3,4‐oxadiazole molecular system.