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Abstract
This accounts introduces unique characteristics by adopting the acyclic diene metathesis (ADMET) polymerization for synthesis of conjugated polymers, poly(arylene vinylene)s, known as promising molecular electronics. The method is more suitable than the other methods in terms of atom efficiency affording defect-free, stereo-regular (exclusive trans) polymers with well-defined chain ends; the resultant polymers possess better property than those prepared by the conventional methods. The chain ends (vinyl group) in the resultant polymer prepared by ruthenium-carbene catalyst(s) can be modified by treating with molybdenum-alkylidene complex (olefin metathesis) followed by addition of various aldehyde (Wittig type cleavage), affording the end-functionalized polymers exclusively. An introduction of initiating fragment, the other conjugated segment, and one-pot synthesis of end-functionalized block copolymers, star shape polymers can be achieved by adopting this methodology.
Highlights
Organic electronics are important emerging technologies, and conjugated polymers like poly(p-arylene vinylene)s are promising materials as novel class of organic semiconductors [1,2,3,4]
Since the resultant polymers prepared by the acyclic diene metathesis (ADMET) polymerization using Ru catalyst possess well-defined chain ends as vinyl group [22,23], a facile, exclusive end-functionalization can be achieved by treating the vinyl groups with molybdenum-alkylidene, Mo(CHCMe2Ph)(N-2,6Me2C6H3)[OCMe(CF3)2]2 (Mo cat.) followed by Wittig-type cleavage with aldehyde [25,26,27,28,29,30,33,34,35]
We have shown that a facile, efficient synthesis of ABCBA type amphiphilic block copolymers has been established in a precise manner by attachment of PEG into the both chain ends of the all-trans, defect-free, high molecular weight PFVs
Summary
Organic electronics are important emerging technologies, and conjugated polymers like poly(p-arylene vinylene)s are promising materials as novel class of organic semiconductors [1,2,3,4]. It has been known that the properties for their device efficiency are generally influenced by their structural regularity, chemical purity, and supramolecular order [1,2,3,4] Both high temperatures (180–300 °C) and vacuum conditions are employed to convert nonconjugated precursor polymers into poly(p-phenylene vinylene)s (PPVs, Scheme 1(1)) [1,5,6]; the synthetic procedure is very sensitive to trace amounts of oxygen during the conversion step that generates oxidation products [5,6]. These structural defects reduce the luminescence quantum efficiency of the final PPV films. Unique characteristics by adopting the ADMET polymerization methods in terms of properties in the resultant polymers as well as synthesis of various advanced materials especially by the end modifications, including the points that have to be taken into consideration for the efficient synthesis, have been introduced
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