Tetraethynylbenzo[2,1,3]thiadiazole

Carlito G. Bangcuyo; Mark D. Smith; Uwe H. F. Bunz

doi:10.1055/s-2003-43356

CLUSTER

Tetraethynylbenzo[2,1,3]thiadiazole

Carlito G. Bangcuyo^a, Mark D. Smith^b, Uwe H. F. Bunz*^a
^a School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA
^b Department of Chemistry and Biochemistry, The University of South Carolina, Columbia, SC 29208, USA
Fax: +1(404)3851795; e-Mail: uwe.bunz@chemistry.gatech.edu;

Abstract

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Abstract

The synthesis and structural characterization of peralkynylated benzothiadiazole 2 is reported. The synthesis utilizes Vollhardt’s access to hexaethynylbenzene by coupling different alkynes to tetrabromobenzo[2,1,3]thiodiazole via the Heck-Cassar-Sonogashira-Hagihara reaction.

Key words

Pd-catalysis - alkynes - heterocycles - peralkynylated π-systems - carbon rich materials

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References

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Crystal Structure Determination: Empirical formula: C₃₀H₃₆N₂S. Formula weight: 456.67. T = 150 (1) K. Wavelength: 0.71073 Å. Crystal system: Monoclinic, P2₁/n. Unit cell dimensions: a = 9.0675 (5) Å, b = 12.4366 (6) Å, c = 24.629 (1) Å, α = 90°; β = 91.740 (1)°; γ = 90°. V = 2776.1 (3) Å³. Z = 4. ρ_calcd = 1.093 g/cm³. Absorption coefficient:
0. 135 mm^-1, F(000): 984. Crystal size: 0.38 × 0.30 × 0.18 mm³. Theta range for data collection: 1.65° to 24.12°. Index ranges: -9 ≤ h ≤ 10, -11 ≤ k≤ 14, -27 ≤ l≤ 28. Reflections collected: 14498. Independent reflections: 4428 [R(int) = 0.0410]. Completeness to Θ = 24.12°, 99.9%. Absorption correction: None. Refinement method: Full-matrix least-squares on F². Data /restraints/parameters: 4428/0/346. Goodness-of-fit on F²: 1.046. Final R indices [I > 2σ(I)]: R1 = 0.0437, wR2 = 0.1177. R indices (all data): R1 = 0.0564, wR2 = 0.1226. Largest diff. peak and hole: 0.319 and -0.202 e Å^-3. Tables and details of the crystal structure determination can be obtained from Cambridge Crystallographic Data Centre (CCDC) utilizing the email deposit@ccdc.cam.ac.uk and the reference number CCDC 222103.

Molecular geometries were determined by AM1 and B3LYP utilizing the 6-31G** basis set. The calculations were carried out with Spartan’04 on a Windows XP platform.