General synthesis, structure, and optical properties of benzothiophene-fused benzoheteroles containing Group 15 and 16 elements

Versatile telluracycle synthesis via the sequential electrophilic telluration of C(sp2)–Zn and C(sp2)–H bonds

“…The compounds 10 , 12 , and 14 , which can be regarded as Te/chalcogen-bridged stilbenes, exhibited a trend of increasing λ max (the longest wavelength absorption maxima) upon changing the extra chalcogen atom from O to Se. This trend is in line with the trends observed for related chalcogen-bridged π-conjugated systems, 25 , 26 and is also consistent with the trend of the lowest transition energies, which are largely represented by the HOMO–LUMO (π–π*) transition (see the ESI † for details). Compound 11 , the cross-conjugated isomer of 10 , showed a distinctly shorter λ max .…”

“…The planar structures of the benzothiophene-fused derivatives 10 and 11 were confirmed using X-ray crystallographic analysis. 19 While 10 adopted a so-called sandwiched herringbone-type packing structure without significant Te–Te interactions (the shortest Te–Te distance being 6.80 Å), 25 11 assumed a herringbone arrangement with close Te–Te contacts (3.71 Å) between the π-stacks ( Fig. 1 ).…”

The Dawn of Functional Organoarsenic Chemistry

“…That is, phosphindole and arsindole showed similar optical properties. The benzothiophene‐fused arsindole was also studied by the same group, who reported that it exhibited the same tendency; its properties were similar to those of the phosphorus analogue. It is expected that arsindole and benzothiophene‐fused arsindole have chirality because of the asymmetric structure and high inversion energy of the arsenic atom.…”

Oxacycle‐Fused [1]Benzothieno[3,2‐b][1]benzothiophene Derivatives: Synthesis, Electronic Structure, Electrochemical Properties, Ionisation Potential, and Crystal Structure

“…Alternately, computational predictions emphasize heteroatom functionalisation of the organic semiconductor core as an efficient pathway in comparison to extension of π conjugated systems in yielding stable and efficient organic semiconductors . This perception has triggered various synthetic advances towards heteroatom containing organic semiconductors, however such modification is rare on BTBT core . In this context we became interested in particularly oxygen containing BTBT ethers, that are expected to have lower oxidation potential which is pertinent in carrier injection aspects of OFETs .…”