13 September 2007 Understanding the mechanisms of photodecarbonylation of the photoprecursors of higher poly(acene)s
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Polyacenes, linear poly(benzenoid) hydrocarbons, are significant compounds for various electronic applications. Smaller lower molecular weight members of the series (anthracene, tetracene, and pentacene) have been extensively investigated for their use as semiconductors, as active layers in organic field-effect transistors (OFETs) and in organic light-emitting diodes (OLEDs). Smaller HOMO-LUMO gaps might be achieved by synthesizing even higher poly(acene)s such as hexacene and heptacene. Nevertheless, an increased instability and insolubility associated with the increasing number of fused rings has become a synthetic challenge for chemists. We have recently developed a photochemical route that allows one to easily synthesize heptacene in rigid media from an α-diketone photoprecursor, thus opening a pathway to utilize these compounds in the construction of suitable devices. Photodecarbonylations of α-diketones are unusual reactions. In most instances, dione excited states become electron transfer acceptors. The decarbonylation is driven by the stability of the resulting aromatic hydrocarbon. We have studied the nature of the excited states involved in photodecarbonylation of the α-diketones and the structure of the carbon monoxide fragment(s). Results obtained on the mechanism of photodecarbonylation investigated using nanosecond flash photolysis and ultra-fast pump-probe techniques are discussed.
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Rajib Mondal, Albert N. Okhrimenko, Bipin K. Shah, Douglas C. Neckers, "Understanding the mechanisms of photodecarbonylation of the photoprecursors of higher poly(acene)s", Proc. SPIE 6658, Organic Field-Effect Transistors VI, 66581B (13 September 2007); doi: 10.1117/12.734788; https://doi.org/10.1117/12.734788

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