Alkynylated Aceno[2,1,3]thiadiazoles

Abstract

Enlarged acenothiadiazoles, which are easily prepared, display attractive optical and electrochemical properties. The annulation of thiadiazole to anthracene gives a stable material with optical properties similar to those of substituted pentacenes.

Effects of electronegative substitution on the optical and electronic properties of acenes and diazaacenes

“…2b) was obtained by LiAlH 4 reduction of 12 (ref. 24) and reacted with 10a-c to furnish the N,N-dihydrodiazapentacenes 14a-c in moderate yields; 14a-c were oxidized by manganese dioxide to give 15a-c after chromatography as green-black, environmentally stable crystalline materials almost quantitatively.…”

“…The absorption spectrum of 11b (in hexane) shows a λ max of 617 nm, whereas 11a, the parent, shows a λ max of 571 nm; that is, the tetrachloro substitution leads to a redshift of 1,306 cm − 1 or 0.16 eV, whereas, in comparison, tetrachloropentacene 6 shows an absorption maximum only 0.032 eV lower in energy than that of the parent compound 5, according to reported UV-Vis spectra (ref. 24).…”

Oligomers and Polymers Based on Pentacene Building Blocks

“…Despite almost a decade of intense research in the field of functionalized pentacene, pentacene 1 still stands among the best functionalized pentacene materials from a device fabrication stand point. The use of silylacetylenes has also been useful for the functionalization of larger acenes, e.g., hexacenes [22] and heptacenes [22,23], as well as smaller acenes like tetracene [24], anthracene [10,25], anthradithiophenes [26], and related chromophores [27,28]. Advances in the synthesis and study of functionalized pentacenes has been reviewed [17,18,19], and will not be discussed further.…”

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

“…11,12 In the case of dibromo derivative 8, the process may be complicated by an exchange of a bromine atom to a chlorine atom. 12 A re-investigation of the synthesis of 1,2,5-thiadiazole-3,4-carbonitrile (10) from diaminomaleonitrile showed that the most probable intermediate is monosulfinylamine 11, which eliminates water by the action of hydrogen chloride formed in the first step of the reaction; 13 In many cases, employing an organic base allows the reaction temperature to be reduced to room temperature, or to 0 • C, avoiding undesirable side processes.…”