Myrtenic acid(3) was prepared by oxidation of α-pinene. Aliphatic bis-thiadiazoles(4a~4h) were prepared by reaction of aliphatic dicarboxylic acids with thiosemicarbazide in the presence of POCl3. Eight novel myrtenal-based bisamide-thiadiazole compounds(5a~5h) were synthesized by condensation of 4a~4h with 3, respectively. The structures were characterized by 1H NMR, 13C NMR, IR and ESI-MS. Antifungal activities test showed that 5a~5h exhibited certain antifungal activities against Fusarium oxysporum f.cucumerinum, Cercospora arachidicola, Physalospora piricola, Alternaria solani and Fusarium graminearumat 50 μg·mL-1. Myrtenal-suberic acid-based bisamide-thiadiazole(5f) had inhibition rate of 60.3% against Physalospora piricola, myrtenal-amber acid-based bisamide-thiadiazole(5b) and myrtenal-sebacic acid-based bisamide-thiadiazole(5h) had inhibition rates of 52.8% and 54.4% against Fusarium graminearum, respectively.
A series of conjugated copolymers(PT-TFQ, PTT-TFQ and PTTT-TFQ) based on fluorinated thiophenequinoxaline(TFQ) were designed and synthesized by Stille reaction using thiophene, 2,2′-bithiophene or 2,2′∶5′,2″-terthiophene as the donor, and the fluorinated quinoxaline thiophene as the receptor, respectively. The structures were characterized by 1H NMR. The effects of different number of thiophene rings on UV-Vis absorption spectra, energy levels, electrochemical behavior and photovoltaic performance were systematically investigated. The results showed that λmax of PT-TFQ, PTT-TFQ and PTTT-TFQ in CHCl3 solution were 545 nm, 578 nm and 649 nm, and exhibited a red shift of 81 nm, 97 nm and 44 nm in film, respectively. The open circuit voltage of PTTFQ, PTTTFQ and PTTTTFQ were 0.86 V, 0.60 V and 0.50 V, and the polymer solar cells based on them exhibited power conversion efficiencies of 3.19%, 3.10% and 2.63%, respectively.
4-Fluoride benzenesulfonamide(2a) and 4-trifluoromethyl benzenesulfonamide(2n) were synthesized by ammonifination from corresponding benzenesulfonyl chloride. A series of substituted phenylisocyanates(4a~4m, 4t, 4I) were obtained by reaction of substituted anilines with triphosgene. Finally, twentyseven novel N-substituted phenyl-4-fluoride(or trifluoromethyl) benzenesulfonylureas were synthesized by condensation of 2 with 4, respectively. The structures were characterized by 1H NMR, IR and ESI-MS.