| This thesis deals with the synthesis of a number of arylene vinylene oligomers that can serve as the electroactive component in numerous semiconductor-based devices. Since the discovery that shorter conjugated systems like oligomers gave significantly better results for oLEDs, gas sensors and other semiconductor applications we soon ceased our attempts to obtain poly(N-methyl-2,5-pyrrylene-vinylene) with pyrrole chemistry, even though the completion of the synthetic procedure to obtain the compound was in sight.; Spectroscopic properties, experimental procedures and characterisation of twenty new substituted arylene vinylene trimers are reported. 2,5-Dimethoxy-1,4-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]benzene (246-OMT) is one of our most succesful trimers for the gas sensor application: doped with perchlorate it results in a sensor with a very long lifetime. Several suggestions for the synthesis of the promising oligomer N-methyl-2,5-bis[2-(2,4,6-trimethoxyphenyl)ethenyl]-pyrrole are given.; The synthesis and interpretation of spectroscopic data of 1,4-bis(2,2-diphenyl-ethenyl)benzene (PEB) and three methoxy substituted PEB oligomers are being described and explained in detail, as is a large quantity of structural data from theoretical calculations, that were applied as an aid for the interpretation of the NMR spectrum of unsubstituted 1,4-bis(2,2-diphenylethenyl)benzene. Based on this unsubstituted PEB we were capable to construct a blue oLED with external quantum efficiency of 0.25%, as well as a white oLED with a quantum efficiency of 0.3%.; Synthesis, characterisation and spectroscopic data of two tetramers, 4,4′-bis[2-(3,4,5-trimethoxyphenyl)ethenyl]stilbene and 4-[2-(2,4,6-trimethoxyphenyl)ethenyl]-4′-[2(4-cyanophenyl)ethenyl]stilbene, are given. They were made for later study of the spectroscopic effects of aggregate formation of these arylene vinylene molecules.; Since many of these arylene vinylene derivatives show potential as active component in some semiconductor applications, we briefly discuss the general working principals of several of these devices and the application-specific conditions for the chemical components. Besides gas sensors (electronic nose) and organic LEDs trimers as e.g. 2,5-dimethoxy-1,4-bis[2-(3,4,5-trimethoxyphenyl)ethenyl]benzene (345-OMT) are used in amperometric and potentiometric liquid electrodes for the detection of specific organic acids and other molecules (electronic tongue), but also as ion-specific electrodes for the detection of lead and cadmium. (Abstract shortened by UMI.)... |
