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X-ray Structural Investigation of Nonsymmetrically and Symmetrically Alkylated [1]benzothieno[3,2-b]benzothiophene Derivatives in Bulk and Thin Films

X-ray Structural Investigation of Nonsymmetrically and Symmetrically Alkylated [1]benzothieno[3,2-b]benzothiophene Derivatives in Bulk and Thin Films

Gabin Gbabode, Michael Dohr, Claude Niebel, Jean-Yves Balandier, Christian Ruzié, Philippe Négrier, Denise Mondieig, Yves H Geerts, Roland Resel, Michele Sferrazza

ACS Appl Mater Interfaces. 2014 Aug 27;6(16):13413-21.

PMID: 25083814

Abstract:

A detailed structural study of the bulk and thin film phases observed for two potential high-performance organic semiconductors has been carried out. The molecules are based on [1]benzothieno[3,2-b]benzothiophene (BTBT) as conjugated core and octyl side groups, which are anchored either symmetrically at both sides of the BTBT core (C8-BTBT-C8) or nonsymmetrically at one side only (C8-BTBT). Thin films of different thickness (8-85 nm) have been prepared by spin-coating for both systems and analyzed by combining specular and grazing incidence X-ray diffraction. In the case of C8-BTBT-C8, the known crystal structure obtained from single-crystal investigations is observed within all thin films, down to a film thickness of 9 nm. In the case of C8-BTBT, the crystal structure of the bulk phase has been determined from X-ray powder diffraction data with a consistent matching of experimental and calculated X-ray diffraction patterns (Rwp = 5.8%). The packing arrangement of C8-BTBT is similar to that of C8-BTBT-C8, that is, consisting of a lamellar structure with molecules arranged in a "herringbone" fashion, yet with lamellae composed of two head-to-head (or tail-to-tail as the structure is periodic) superimposed molecules instead of only one molecule for C8-BTBT-C8. As for C8-BTBT-C8, we demonstrate that the same phase is observed in bulk and thin films for C8-BTBT whatever the film thickness investigated.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP583050708	C8-BTBT		583050-70-8	Price

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