Abstract
The redox potentials of 4,4’-dimethyl-N’N’-alkylidene bridged 2,2’-bipyridinium salts derivatives (DBPAs) can be controlled by changing the N, N’-alkylidene bridge length which changes the conformation of the DBPAs.. In this paper, the torsional angles between the two pyridine rings and the molecular energy of DBPAs are calculated using a PC based software package (AccuModel 1.2). The relationship between torsional angle and N, N’-alkylidene bridge length is discussed. The molecular energy of DBPAs can also be related to the torsional angles (or N, N’-alkylidene bridge size). Some DBPAs had been synthesized and their redox potentials measured. The difference in potential between ethylene and propylene bridged DBPAs is large enough to make a organic diode through bilayer modified electrode.
Highlights
Bilayer modified electrodes with an unidirectional electron flow property are of interest for their potential use in understanding energy transfer in plants or animals and their applications for the preparation of organic solar cells
The electron density on the redox center is affected by the substituents present, as the redox potentials of the resultant chemicals depend on the electron density
We found that 2, 2’bipyridine derivatives could react with alkyl dibromides to form N, N’-alkylidene bridged bis-salt derivatives and that these display good reversibility
Summary
Bilayer modified electrodes with an unidirectional electron flow property are of interest for their potential use in understanding energy transfer in plants or animals and their applications for the preparation of organic solar cells. A redox potential difference on the same redox center was obtained by three methods [2,3,4]: 1). When we used 1, 2-dibromoethane and 1, 3dibromopropane reacted with 4, 4’-dimethyl-2, 2’-bipyridine respectively, the resulting DBPA compounds (Figure 1) show redox potentials of 0.44 V and 0.66 V vs SCE respectively. That the torsional angle is formed and controlled by the N, N’-alkylidene bridge between two nitrogen atoms.
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