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We have synthesized 13,13'-(3,5-bis(trifluoromethyl)phenyl)-6,6'-bipentacene from a soluble bispentacenequinone precursor. Bispentacene takes orthogonal conformation in the solid state and exhibits four reversible redox potentials. In addition, a tetracyanobipentacenequinodimethane was obtained for the first time from the pure bispentacenequinone.

The metal-free and meso-free [14]triphyrin(2.1.1) compound was successfully prepared based on the intramolecular McMurry coupling reaction of diformyl-tripyrrane in 16% yield, and was converted to the bowl-shaped Mn(i)(TriP)(CO)3 and Re(i)(TriP)(CO)3.

A series of benzoporphycenes and naphthoporphycenes and their zinc complexes were prepared from bicyclo[2.2.2]octadiene fused porphycenes by a retro-Diels-Alder reaction and their photophysical properties were studied. Free-base tetranaphthoporphycene was not soluble in common organic solvents, but zinc tetranaphthoporphycene was slightly soluble in pyridine and showed B- and Q-bands at 507 and 690 nm, respectively. Dinaphthoporphycene showed broad B- and Q-bands due to its lower symmetry. Tetrabenzo-, dibenzo-, and dinaphthoporphycenes showed fluorescence at 673, 654, and 670 nm with quantum yields of 0.32, 0.42, and 0.31, respectively, although their precursors were non-fluorescent. Zinc complexes of tetrabenzo-, dibenzo-, tetranaphtho-, dinaphthoporphycenes and their bicyclo[2.2.2]octadiene-fused precursors revealed moderate fluorescence with quantum yields of 0.15-0.37. The crystal structures of tetrabenzo- and dibenzoporphycenes showed herringbone structures, while the zinc tetrabenzoporphycene showed a hexagonal box-structure with six pyridine ligands inside.

Novel bisimide-fused acenes were synthesized viabismuth triflate mediated double-cyclization reaction of acid chlorides and isocyanates. Their optical and electrical properties revealed significantly smaller HOMO-LUMO gaps compared with those of their parent acenes. Fabricated OFET based on tetracene bisimide showed n-type OFET outputs.

Boron complexes of [14]triphyrins(2.1.1) were prepared from free-base [14]triphyrins(2.1.1) with phenylboron dichloride. The absorption spectrum of the meso-free [small beta]-alkyl-triphyrin boron complex in CH2Cl2 showed a broad weak band at around 640 nm assigned to transition from B-phenyl to the triphyrin, while that of the meso-aryl benzotriphyrin boron complex showed only Soret and Q bands.

The non-luminous precursor, 2-(1-pyrenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dione, was photochemically converted to highly-fluorescent 2-(1-pyrenyl)anthracene quantitatively in solution and in the PMMA film and the fluorescence quantum yield of the acene in benzonitrile was as high as 0.99.

P-n junction solar cells based on anthradithiophene (ADT) as a p-type semiconductor were fabricated by using the photoprecursor method in which an [small alpha]-diketone-type precursor was spin-coated and then transformed to ADT in situ by photoirradiation. Combination with PC71BM as an n-layer material led to 1.54% photoconversion efficiency.