Crystal packing motifs of oligothiophenes end-capped with N-containing aryls

Oligothiophenes (OThs) end-capped with 3-quinolyl or pyridyl with nitrogen atom at meta-, ortho- or para-position were synthesized. The single-crystal structures of the resulting molecules, i.e., o-PyTh4, m-PyTh4, p-PyTh4, QuTh2, and QuTh3, were successfully determined by single-crystal X-ray analysis. Pyridyl end-capped OThs; o-PyTh4, m-PyTh4, and p-PyTh4, adopt the different herringbone packing arrangement in crystals depending on the position of the nitrogen atom because of the presence of weak C-H center dot center dot center dot N hydrogen bonds. The p-PyTh4 molecules are linked each other along the long axis of the molecules to form the extended chains by C-H center dot center dot center dot N dimer synthon. For m-PyTh4, the C-H center dot center dot center dot N interactions two-dimensionally extend through C-H center dot center dot center dot N trimer synthon.

Naphthyl and thionaphthyl end-capped oligothiophenes as organic semiconductors: Effect of chain length and end-capping groups

Two series of oligothiophenes (OThs), NaTn and TNTn (n = 2-6 represents the number of thiophene rings), end-capped with naphthyl and thionaphthyl units have been synthesized by means of Stille coupling. Their thermal properties, optical properties, single crystal structures, and organic field-effect transistor performance have been characterized. All oligomers display great thermal stability and crystallinity. ne crystallographic structures of NaT2, NaT3, TNT2, and TNT3 have been determined. The crystals of NaT2 and NaT3 are monoclinic with space group P2(1)/C, while those of TNT2 and TNT3 are triclinic and orthorhombic with space groups P-1(-) and P2(1)2(1)2(1), respectively. All oligomers adopt the well-known herringbone packing-mode in crystals with packing parameters dependent on the structure of the end-capping units and the number of thiophene rings. The shorter intermolecular distance in NaT3 compared to NaT2 indicates that the intermolecular interaction principally increases with increasing molecular length. X-ray diffraction and atomic force microscopy (AFM) characterization indicate that the NaTn oligomers can form films with better morphology and high molecular order than TNTn oligomers with the same number of thiophene rings. The NaTn oligomers exhibit mobilities that are much higher than those for TNTn oligomers (0.028-0.39 cm(2) V-1 s(-1) versus 0.010-0.055 cm(2) V-1 s(-1), respectively).

Syntheses and Crystal Structures of Fused Thiophenes: [7]Helicene and Double Helicene, a D-2-Symmetric Dimer of 3,3 '-Bis(dithieno[2,3-b:3 ',2 '-d]thiophene)

The efficient synthesis of (TMS)(2)-[7]helicene (rac-3) and double helicene, a D-2-symmetric dimer of 3,3'-bis(dithieno-[2,3-b:3',2'-d]thiophene) (rac-4) was developed. The crystal structures of 3 and 4 show both strong intermolecular pi-pi interactions and S center dot center dot center dot S interactions. UV/vis spectra reveal that both 3 and 4 show significant pi-electron delocalization.

Synthesis and characterization of monodisperse oligo(fluorene-co-bithiophene)s

A series of monodisperse oligo(9,9-di-n-octylfluorene-co-bithiophene)s (OFbTs) with molecular lengths of up to 19.5 nm and molecular weights up to 7025 g mol(-1) has been synthesized by a divergent/convergent approach involving Stille coupling reactions. Stille coupling is quite efficient in preparing this class of oligomers, and even the molecule with nine fluorene units and eight bithiophene units (F9Th16) can be synthesized in a yield as high as 70%. Because of easy functionalization of the thiophene ring at its alpha position, no additional protecting group allowing activation for further reaction is necessary. However, the synthetic routes must be optimized to eliminate contamination of the targeting compounds with the homocoupling product of the organotin reagents. Synthesis of the longest oligomer F13Th24 in a relative large quantity is limited by its low yield due to the pronounced ligand-exchange side reactions of the starting materials and reaction intermediates. All oligomers longer than F4Th6 are nematic mesomorphs and exhibit enhanced glass transition temperature and clearing point with increasing molecular length, as revealed by differential scanning calorimetry and polarizing optical microscopy.

Efficient synthesis of trimethylsilyl-substituted dithieno[2,3-b:3',2'-d]thiophene,tetra[2,3-thienylene] and hexa[2,3-thienylene] from substituted [3,3']Bithiophenyl

Efficient synthetic procedures for the preparation of beta-trithiophenes (dithieno[2,3-b:3',2'-d]thiophene) and two macrocyclic compounds, tetra[2,3-thienylene] and hexa[2,3-thienylene] bearing trimethylsilyl (TMS) groups from 2,2'-dibromo-5,5'-bistrimethylsilanyl[3,3']bithiophenyl are reported. The UV-Vis spectra property and crystal structures of these macrocyclic oligothiophenes are described.

Naphthyl end-capped quarterthiophene: A simple organic semiconductor with high mobility and air stability

An organic semiconductor that can be mass produced is synthesized by end-capping quaterthiophene with naphthyl units (NaT4). An organic thin-film transistor (OTFT, see figure) has been fabricated using this organic semiconductor, and exhibits stability under ambient conditions with a mobility of up to 0.40 cm(2) V-1 s(-1).

Improved n-type organic transistors by introducing organic heterojunction buffer layer under source/drain electrodes

N-type organic thin-film transistors (OTFTs) employing hexadecafluorophthalocyaninatocopper (F16CuPc) as active layer and p-type copper phthalocyanine (CuPc) as buffer layer are demonstrated. The highest field-effect mobility is 7.6x10(-2) cm(2)/V s. The improved performance was attributed to the decrease of contact resistance due to the introduction of highly conductive F16CuPc/CuPc organic heterojunction. Therefore, current method provides an effective path to improve the performance of OTFTs.