Synthesis, Crystal Structure, and Transistor Performance of Tetracene Derivatives

Department of Chemical Engineering, Stanford University, Palo Alto, California, United States
Journal of the American Chemical Society (Impact Factor: 12.11). 01/2005; 126(47):15322-3. DOI: 10.1021/ja045208p
Source: PubMed


The substitution of chloro or bromo groups in tetracene gives rise to the change of crystal structure, having a substantial effect on carrier transport. Halogenated tetracene derivatives were synthesized and grown into single crystals. Monosubstituted 5-bromo- and 5-chlorotetracenes have the herringbone-type structure, while 5,11-dichlorotetracene has the slipped pi stacking structure. Mobility of 5,11-dichlorotetracene was measured to be as high as 1.6 cm2/V.s in single-crystal transistors. The pi stacking structure, which enhances pi orbital overlap and facilitates carrier transport, may thus be responsible for this high mobility.

1 Follower
18 Reads
  • [Show abstract] [Hide abstract]
    ABSTRACT: Novel pi-electron systems with trifluoromethylphenyl groups and/or a thiazolothiazole unit were developed as n-type semiconductors for OFETs. They showed excellent n-type performances with high electron mobilities. The trifluoromethylphenyl group was found to be very effective in inducing n-type behavior. The thiazolothiazole unit was favorable for forming stacking structures leading to efficient intermolecular pi-pi interactions.
    Journal of the American Chemical Society 05/2005; 127(15):5336-7. DOI:10.1021/ja042219+ · 12.11 Impact Factor
  • [Show abstract] [Hide abstract]
    ABSTRACT: The quest for high-performance organic thin-film transistor (OTFT) gate dielectrics is of intense current interest. Beyond having excellent insulating properties, such materials must meet other stringent requirements for optimum OTFT function: efficient low-temperature solution fabrication, mechanical flexibility, and compatibility with diverse gate materials and organic semiconductors. The OTFTs should function at low biases to minimize power consumption, hence the dielectric must exhibit large gate capacitance. We report the realization of new spin-coatable, ultrathin (<20 nm) cross-linked polymer blends exhibiting excellent insulating properties (leakage current densities approximately 10(-)(8) Acm(-)(2)), large capacitances (up to approximately 300 nF cm(-)(2)), and enabling low-voltage OTFT functions. These dielectrics exhibit good uniformity over areas approximately 150 cm(2), are insoluble in common solvents, can be patterned using standard microelectronic etching methodologies, and adhere to/are compatible with n(+)-Si, ITO, and Al gates, and with a wide range of p- and n-type semiconductors. Using these dielectrics, complementary invertors have been fabricated which function at 2 V.
    Journal of the American Chemical Society 07/2005; 127(29):10388-95. DOI:10.1021/ja052488f · 12.11 Impact Factor
  • Source
    [Show abstract] [Hide abstract]
    ABSTRACT: Charge transport characteristics for metal-molecule-metal junctions containing two structurally related pi-conjugated systems were studied to probe pi-pi interactions in molecular junctions. The first molecule contains a typical pi-conjugated framework derived from phenylene vinylene units, whereas the second has the phenylene vinylene structure interrupted by a [2.2]paracyclophane (pCp) core. Electrochemical investigations were used to characterize the defects and packing density of self-assembled monolayers of the two molecules on gold surfaces and to enable quantitative comparison of their transport characteristics. Current-voltage measurements across molecular junctions containing the two species demonstrate that the pCp moiety yields a highly conductive break in through-bond pi-conjugation. The observed high conductivity is consistent with density functional theory calculations, which demonstrate strong through-space pi-pi coupling across the pCp moiety.
    Proceedings of the National Academy of Sciences 07/2005; 102(25):8821-5. DOI:10.1073/pnas.0500002102 · 9.67 Impact Factor
Show more