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Abstract: 2,3-Diamino-9,9-dioctylfluorene (DADOF), as a new multifunctional intermediate for π conjugated molecules, was efficiently synthesized via a seven-step procedure with an overall yield of 30%. Novel 9,9-dihydro-9,9-dioctyl-2-phenylfluoreno[3,2-d]imidazole (DOFIPh)-type fluorophores with polar substituents were designed and conveniently synthesized from DADOF, and their absorption and fluorescence properties were investigated in solution and in the solid state. The fluorophore DOFIPh exhibits strong blue emission in solid state and fine-tuning of the emission is possible depending on the electronic nature of the substituents. [Copyright &y& Elsevier]

Abstract: A series of 10,10-dioctyl-3,6-dihydrofluoreno[2,3-d:6,7-d′]diimidazole derivatives were conveniently synthesized by condensation of the key intermediate 2,3,6,7-tetraamino-9,9-dioctylfluorene (TADOF) with aldehydes under very mild conditions. All of the target compounds were characterized using 1H NMR, 13C NMR, and elemental analysis. The crystal structure of 3,6-dibenzyl-10,10-dioctyl-2,7-diphenyl-6,10-dihydro-3H-fluoreno[2,3-d:6,7-d′]diimidazole was determined as triclinic, space group P-1 type, using single X-ray crystallography. For seventeen samples, UV–visible absorption maximum wavelength (λ max), fluorescence excitation wavelength (λ ex), fluorescence emission wavelength (λ em) and fluorescence quantum yield (φ FL) were measured in dilute dichloromethane solution and in the solid state. These compounds possess a medium strong blue fluorescence-emitting ability with φ FL values in the region of 0.30–0.89 and structure-optical behavior characteristics were discussed. [Copyright &y& Elsevier]