Synthesis and Characterization of Fullerene and Single Walled Carbon NanoTubes Derivatives with Triphenylamine Moiety, and Their Applications

Due to triphenylamine (TPA) with good hole transport, and electron-rich properties, we try to introduce this moiety onto the fullerene to investigate the electrochemical properties and the performance of photovoltaic devices. Besides, TPA with electroactive properties, we also functionalize single walled carbon nanotubes (SWCNTs) with TPA derivative to explore the behavior of electropolymerization. Moreover, we functionalize SWCNTs with thiol groups to study the self assembly behavior. In chapter 2, we synthesize fullerene derivatives H-C60 mono 5a and H-C60 di 6a with TPA moiety. We discuss the electrochemical behavior of fullerene derivatives and the electrochemical properties of the polymeric films. We find that the polymeric films have the electrochemical memory in DMF. In chapter 3, we synthesize fullerene derivatives with TPA moiety containing para methyl substitution, Me-C60 mono 5b and Me-C60 di 6b. We study the performance of photovoltaic devices based on P3HT : fullerene derivatives with various blend ratios and casting solvents. The device of P3HT : Me-C60 mono 5b with the blend ratio 1 : 0.7 in a mixed solvent of ODCB and TCB showed high open circuit voltage (Voc) of 0.69 V under the illumination of AM 1.5G, 100 mW/cm2 with high power conversion efficiency (PCE) of 3.16 %. The device of P3HT : Me-C60 di 6b (1 : 1) shows even higher Voc of 0.87 V with the PCE of 1.83 %. In chapter 4, we combine the good merits of PCBM with higher Jsc and Me-C60 di 6b with higher Voc. This is the first time to tune Voc by adding Me-C60 di 6b as a dopant. We find the correlation between Voc and the blend ratios of PCBM to Me-C60 di 6b. In chapter 5, we investigate ternary mixing consisting of poly(3-hexythiophene) (P3HT), PCBM and Me-C60 mono 5b. From the changes of optical micrography, TEM images, UV-Vis absorption, and photoluminescence , we find that thermal stability of polymer solar cells with the addition 10 % of Me-C60 mono 5b are remarkly enhanced by supressing the destructive phase segregation between the polymer and fullerene. For ternary films, there are no significant degradation in morphology or performance even after 15 hr annealing at 160 oC, where the performance of devices based on PCBM or based on Me-C60 mono 5b degraded dramatically against long-time annealing. In chapter 6, we synthesize a series of soluble single walled carbon nanotube derivatives by amidation. We investigate the self assembly behavior between Au substrate and gold nanoperticles and thiol- functionalized nanotubes (2-4). The gold nanoparticles are sticking not only at the terminal, but also on the side-wall of SWCNT. Further, we can purify and separate from higher molecular weight by GPC. Besides, we synthesize SWCNT with TPA moiety (2-6) can proceed the electropolymerization while applying potential