Conjugated thiophene-containing oligoacenes through photocyclization: Bent acenedithiophenes and a thiahelicene

TY - JOUR

T1 - Conjugated thiophene-containing oligoacenes through photocyclization

T2 - Bent acenedithiophenes and a thiahelicene

AU - Patrick, Brian O.

AU - MacLachlan, Mark J.

AU - Wolf, Michael O.

PY - 2009/7/17

Y1 - 2009/7/17

N2 - (Graph Presented) The preparation of bent anthradithiophenes (BADTs) using an oxidative photocyclization-based synthetic strategy is reported. The optical properties of the new compounds were characterized by UV-vis and fluorescence spectroscopies, and the redox properties were probed by cyclic voltammetry. Structural studies using single crystal X-ray crystallography show that the unsubstituted BADT adopts a slipped cofacial stacking arrangement in the solid state with π-π interactions along the intermolecular stacking axis. The dialkylated derivatives adopt similar packing motifs with varying degrees of slipping along their long and short molecular axes while the diphenyl derivative packs into an edge-to-face herringbone arrangement. Powder diffraction data show that in thin films prepared by vacuum evaporation, molecules of the unsubstituted BADT are oriented nearly perpendicular to the substrate surface whereas the dialkylated derivatives adopt either multiple phases or new polymorphs. A thiahelicene prepared from the oxidative photocyclization of two isomers of 2,5-dithienyl-1,4-distyrylbenzene is described and the crystal structure reported.

AB - (Graph Presented) The preparation of bent anthradithiophenes (BADTs) using an oxidative photocyclization-based synthetic strategy is reported. The optical properties of the new compounds were characterized by UV-vis and fluorescence spectroscopies, and the redox properties were probed by cyclic voltammetry. Structural studies using single crystal X-ray crystallography show that the unsubstituted BADT adopts a slipped cofacial stacking arrangement in the solid state with π-π interactions along the intermolecular stacking axis. The dialkylated derivatives adopt similar packing motifs with varying degrees of slipping along their long and short molecular axes while the diphenyl derivative packs into an edge-to-face herringbone arrangement. Powder diffraction data show that in thin films prepared by vacuum evaporation, molecules of the unsubstituted BADT are oriented nearly perpendicular to the substrate surface whereas the dialkylated derivatives adopt either multiple phases or new polymorphs. A thiahelicene prepared from the oxidative photocyclization of two isomers of 2,5-dithienyl-1,4-distyrylbenzene is described and the crystal structure reported.

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U2 - https://doi.org/10.1021/jo900590u

DO - https://doi.org/10.1021/jo900590u

M3 - Article

C2 - 19469525

SN - 0022-3263

VL - 74

SP - 4918

EP - 4926

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 14

ER -