4,4′-Bis[2-(3,4-dibutyl-2-thienylethyn­yl)]biphen­yl

Lei Liu; Na Liu; Wei Xu; Dao-Ben Zhu

doi:10.1107/S1600536808036143

. 2008 Nov 13;64(Pt 12):o2306. doi: 10.1107/S1600536808036143

4,4′-Bis[2-(3,4-dibutyl-2-thienylethynyl)]biphenyl

Lei Liu ^a,^*, Na Liu ^b, Wei Xu ^c, Dao-Ben Zhu ^b

PMCID: PMC2959992 PMID: 21581283

Abstract

The molecule of the title compound, C₄₀H₄₆S₂, reveals C _i symmetry. An inversion centre is located at the mid-point of the C—C bond of the biphenyl unit; the asymmetric unit comprises one-half of the molecule. The conjugated backbone is nearly planar, with a mean deviation of 0.041 Å.

Related literature

For general background, see: Brad Wan et al. (2000 ▶); Cornil et al. (2001 ▶); Grosshenny et al. (1997 ▶); Huang & Tour (1998 ▶); Tour (1996 ▶). For related structures, see: Baudour (1972 ▶); Charbonneau & Delugeard (1977 ▶); Domenicano et al. (1975 ▶); Robertson (1961 ▶). For the synthesis, see: Liu et al. (2005 ▶).

Experimental

Crystal data

C₄₀H₄₆S₂
M _r = 590.89
Triclinic,
a = 9.2040 (18) Å
b = 9.3640 (19) Å
c = 10.582 (2) Å
α = 85.69 (3)°
β = 85.18 (3)°
γ = 69.41 (3)°
V = 849.7 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 (2) K
0.62 × 0.40 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995 ▶) T _min = 0.805, T _max = 0.992
3595 measured reflections
3595 independent reflections
2287 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.241
S = 1.07
3595 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 2001 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks 070712a, I. DOI: 10.1107/S1600536808036143/kp2189sup1.cif

e-64-o2306-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036143/kp2189Isup2.hkl

e-64-o2306-Isup2.hkl^{(175.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The present research work was financially supported by the National Natural Science Foundation of China (grant No. 20572113), Hebei Natural Science Foundation, and the Hebei University of Science and Technology Project for Young Scientists Fund.

supplementary crystallographic information

Comment

The synthesis and characterization of nanometer-sized conjugated molecules of precise length and constitution are of widespread interest, which is due to their electroconductive, magnetic, and optical properties (Tour, 1996; Huang & Tour, 1998; Grosshenny et al., 1997; Brad Wan et al., 2000). Generally, crystal structure of a molecule is important for better understanding of its properties. Therefore, structures of oligothiophene single crystals have been reported. The field of molecular organic semiconductors is being revolutionized by the availability of ultrahigh purity single crystals that have allowed the demonstration of phenomena long thought to be restricted to inorganic semiconductors (Cornil et al., 2001).

The molecule of the title compound (Fig. 1) is centrosymmetric. An asymmetric unit comprises a half on the molecule. The inversion centre is located in the middle of C3—C3i bond. Conjugated molecular skeleton is nearly planar; mean deviation from the best least-square plane is 0.041 Å. The endocyclic bond angles on the long molecular axis are less than the normal 120° value (they vary from 116.42–117.52°) whereas that situated out of this long molecular axis are greater than 120° (in the range 120.73–122.43°). This result agrees with those obtained for polyphenyls (Robertson, 1961; Baudour, 1972; Domenicano et al., 1975; Charbonneau & Delugeard, 1977). The two thiophene rings, phenyl rings and C≡C are coplanar. The crystal packing is dominated by van der Waals interactions.

Experimental

The synthesis of 4,4'-bis-[2-(3,4-dibutyl-2-thienylethynyl)]biphenyl was performed as previously described (Liu et al., 2005).

Yellow needles were grown from an ethanol/hexane solution by slow evaporation.