A 10,20-bis(triisopropylsilylethynyl)tetrabenzo-5,15-diazaporphine (TIPS-TBDAP) was synthesized by the metal-template aza-annulation reaction. TIPS-TBDAP showed intense far-red fluorescence at 723 nm with a fluorescence quantum yield of 31% in chloroform solution. X-ray diffraction analysis revealed that TIPS-TBDAP forms a one-dimensional slipped [Formula: see text]-stacking structure in the single crystal state. TIPS-TBDAP is soluble in common organic solvents owing to the bulky substituents and solution-processed field-effect transistors (FETs) could be fabricated. Dip-coating and single-crystal FETs showed the maximum hole mobilities of 1.5× 10[Formula: see text] and 0.16 cm2 V[Formula: see text] s[Formula: see text], respectively.
We report improved synthesis of the bicyclo[2.2.2]octadiene(BCOD)-fused 5,15-diazaporphyrin and meso-substituted derivatives by metal-template aza-annulation reaction. The obtained compounds act as the soluble precursors of tetrabenzo-5,15-diazaporphyrin (TBDAP) by thermal conversion. The substituents at meso-positions make significant differences in the optical properties and morphology in the thin film upon thermal conversion.
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