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1.
Chemistry ; 19(11): 3721-8, 2013 Mar 11.
Article in English | MEDLINE | ID: mdl-23362156

ABSTRACT

Three new benzothieno[3,2-b]thiophene (BTT; 1) derivatives, which were end-functionalized with phenyl (BTT-P; 2), benzothiophenyl (BTT-BT; 3), and benzothieno[3,2-b]thiophenyl groups (BBTT; 4; dimer of 1), were synthesized and characterized in organic thin-film transistors (OTFTs). A new and improved synthetic method for BTTs was developed, which enabled the efficient realization of new BTT-based semiconductors. The crystal structure of BBTT was determined by single-crystal X-ray diffraction. Within this family, BBTT, which had the largest conjugation of the BTT derivatives in this study, exhibited the highest p-channel characteristic, with a carrier mobility as high as 0.22 cm(2) V(-1) s(-1) and a current on/off ratio of 1×10(7) , as well as good ambient stability for bottom-contact/bottom-gate OTFT devices. The device characteristics were correlated with the film morphologies and microstructures of the corresponding compounds.


Subject(s)
Thiophenes/chemical synthesis , Transistors, Electronic , Crystallography, X-Ray , Models, Molecular , Molecular Structure , Thiophenes/chemistry
2.
Chemphyschem ; 14(12): 2772-6, 2013 Aug 26.
Article in English | MEDLINE | ID: mdl-23776039

ABSTRACT

A solution-processed anthradithiophene derivative, 5,11-bis(4-triethylsilylphenylethynyl)anthradithiophene (TESPE-ADT), is studied for use as the semiconducting material in thin-film transistors (TFTs). To enhance the electrical performance of the devices, two different kinds of solution processing (spin-coating and drop-casting) on various gate dielectrics as well as additional post-treatment are employed on thin films of TESPE-ADT, and p-channel OTFT transport with hole mobilities as high as ~0.12 cm(2) V(-1) s(-1) are achieved. The film morphologies and formed microstructures of the semiconductor films are characterized in terms of film processing conditions and are correlated with variations in device performance.

3.
Langmuir ; 26(16): 13353-8, 2010 Aug 17.
Article in English | MEDLINE | ID: mdl-20695577

ABSTRACT

In situ scanning tunneling microscopy (STM) was used to reveal the structures of dithieno[2,3-b:3,2-d]thiophene diphenyl (DTT) molecules deposited onto Au(111) electrode from a dosing solution made of dichlorobenzene and 50 muM DTT. Potential control was proven to be of prime importance in guiding the arrangement of DTT admolecules on Au(111) in 0.1 M HClO(4), as disorder DTT adlayer seen at E > 0.3 V (vs reversible hydrogen electrode) was transformed into a highly ordered (2 x 7 square root(3))rect -2DTT structure when the potential was made to 0.05 to 0.2 V. The ordered structure was stable for hours between 0.05 and 0.2 V. However, switching the potential further negative to 0 V resulted in slow melting of the ordered structure. The (2 x 7 square root(3))rect-DTT ordered adlattices recuperated when the potential was made positive to 0.2 V. Internal molecular functionalities of the thienothiophene and benzene in DTT admolecules were clearly discerned, from which the lateral structure for the (2 x 7 square root(3))rect-2DTT structure and registries of admolecules were deduced. The dynamics of the DTT adlattices on the Au(111) electrode surface was examined by real-time STM imaging, showing reorientation of as many as 150 DTT admolecules to join a neighboring ordered array within minutes.

4.
ACS Appl Mater Interfaces ; 4(12): 6992-8, 2012 Dec.
Article in English | MEDLINE | ID: mdl-23218927

ABSTRACT

Three benzo[d,d']thieno[3,2-b;4,5-b']dithiophene (BTDT) derivatives, end-functionalized with benzothiophenyl (BT-BTDT; 2), benzothieno[3,2-b]thiophenyl (BTT-BTDT; 3), and benzo[d,d']thieno[3,2-b;4,5-b']dithiophenyl (BBTDT; 4), were prepared for bottom-contact/bottom-gate organic thin-film transistors (OTFTs). An improved one-pot [2 + 1 + 1] synthetic method of BTDT with improved synthetic yield was achieved, which enabled the efficient realization of new BTDT-based semiconductors. All of the BTDT compounds exhibited high performance p-channel characteristics with carrier mobilities as high as 0.34 cm(2)/(V s) and a current on/off ratio of 1 × 10(7), as well as enhanced ambient stability. The device characteristics have been correlated with the film morphologies and microstructures of the corresponding compounds.

5.
Langmuir ; 25(17): 9887-93, 2009 Sep 01.
Article in English | MEDLINE | ID: mdl-19518130

ABSTRACT

In situ scanning tunneling microscope (STM) was used to examine the spatial structures of pentacene molecules adsorbed onto a Au(111) single-crystal electrode from a benzene dosing solution containing 16-400 microM pentacene. Molecular-resolution STM imaging conducted in 0.1 M HClO(4) revealed highly ordered pentacene structures of ( radical31 x radical31)R8.9 degrees , (3 x 10), ( radical31 x 10), and ( radical7 x 2 radical7)R19.1 degrees adsorbed on the reconstructed Au(111) electrode dosed with different pentacene solutions. These pentacene structures and the reconstructed Au(111) substrate were stable between 0.2 and 0.8 V [vs reversible hydrogen electrode, RHE]. Increasing the potential to E > 0.8 V lifted the reconstructed Au(111) surface and disrupted the ordered pentacene adlattices simultaneously. Ordered pentacene structures could be restored by applying potentials negative enough to reinforce the reconstructed Au(111). At potentials negative of 0.2 V, the adsorption of protons became increasingly important to displace adsorbed pentacene admolecules. Although the reconstructed Au(111) structure was not essential to produce ordered pentacene adlayers, it seemed to help the adsorption of pentacene molecules in a long-range ordered pattern. At room temperature (25 degrees C), approximately 100 pentacene molecules seen in STM images could rotate and align themselves to a neighboring domain in 10 s, suggesting that pentacene admolecules could be mobile on Au(111) under the STM imaging conditions of -150 mV in bias voltage and 1 nA in feedback current.

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