Chalcogenoarene semiconductors: new ideas from old materials

Abstract

There are certain aspects of the electronic and packing behavior of planar aromatic molecules containing exocyclic chalcogen atoms (i.e., sulfur, selenium, tellurium) which need considerable re-enlightenment. This class of semiconductors was once regarded as next-generation p-donors for applications in charge-transfer complexes. With the advent of new device technologies such as lightemitting diodes, solar cells, and organic transistors, the interest in charge-transfer complexes eventually tapered off. However, significant progress in the use of this class of materials in modern organic devices has been reported over the last five years. In this article, we review the exocyclic arenes with chalcogen atoms in peri-positions, summarize synthetic routes to these compounds and take a close look at their basic properties. Particular emphasis is placed upon their packing arrangements and the effect of exocyclic chalcogen atoms on the crystal packing motifs. Selected example applications from this class of materials in different fields will be highlighted. As a final note, we provide a prediction for their use in mainstream applications such as energy and fundamental charge transport/generation.

Anisotropic charge carrier transport of optoelectronic functional selenium‐containing organic semiconductor materials

“…Therefore, differing from other SeSe‐containing compounds which only present p‐type OSCs feature, Compound 12 could be a promising ambipolar OSCs. The λ h is lower than the λ e in most of the compounds except for Compounds 4 , 8 , and 12 , which are coincident with the previous results . So, we can infer that Compounds 4 , 8 , and 12 may have relative large electron mobility.…”

“…The λ h is lower than the λ e in most of the compounds except for Compounds 4, 8, and 12, which are coincident with the previous results. [27,72] So, we can infer that Compounds 4, 8, and 12 may have relative large electron mobility.…”

“…[10,[19][20][21][22] Several reviews have overviewed the packing patterns, electronic structures, and transport property of thienoacene-based OSCs. [23][24][25][26][27] Materials containing selenium, as the same family element of sulfur, are also proved to act as high-performance OSCs with the hole mobility reaching 2.66 m 2 V −1 s −1 for single crystal transistors and 1.9 cm 2 V −1 s −1 for thin-film transistors. [28,29] However, few works focusing on the investigation of selenium-containing OSCs which probably could be used as n-type or ambipolar OSCs.…”

Seleno groups control the energy-level alignment between conjugated organic molecules and metals

“…24,25 In these salts TSeT acts as donor, and it was shown by electrochemical measurements and calculations that the IE of tetracene decreases significantly by the selenium substitution (even below that of pentacene). 26 With our photoemission results on vacuum-deposited TSeT thin films on the (111)-surfaces of coinage metals we demonstrate that it is indeed possible to combine the special energy-level alignment situation of SAMs with the organic semiconductor properties of TSeT, resulting in extremely small HIBs.…”

Pyrrole‐Modified Subporphyrins Bearing a Sulfur‐Containing Heterocyclic Unit

“…The S-S bond lengths are 2.110(2) A in 8 and 2.1045(9) A in 9, which are similar to those of disulfide-appended polyaromatic hydrocarbons. [26] [27] The C(a)-N-C(a) bond angles in the dithiazole units of 8 and 9 are 124.5(3)°a nd 121.6(2)°, respectively, being significantly larger than those in the pyrrole units (111.6(3) -113.2(2)°) and comparable to that in the aldimine unit of 1 (123.9(1)°). [21] The C(a)-N-C(a) bond angles in the dithiazine unit of 6 and the 2-oxodithiazine unit of 7 are even larger (129.3(4)°and 128.6(1)°, respectively), probably due to the six-membered ring structures.…”