Synthesen, chemische und elektrische Eigenschaften von Tetrathiafulvalen mit 1,6‐Methano[10]annulen‐Partialstruktur und von Chalcogendiimid‐derivaten

Abstract

Goehring, Heidelberg, mit herzlichen Wiinschen zum 70,Geburtstag gewidmet (22.VIlI.X3) Syntheses, Chemical and Electrical Properties of Tetrathiafulvalene with a 1,6-MethanollOJannulene Moiety and of Chalcogendiimide-Derivatives SummuryThe synthesis o f the tetrathiafulvalene 6 has been described: the reaction of' I with the benzenedithiol 2 yielded the bis-dithioacetal 3 of 1,6-rnethano[ 101annulene-dicarbaldehyde 1. The oxidation of 3 in the presence of HBF, in Et,O yielded the salt 4, elimination of a hydride anion with triphenylmethylium tetrafluoroborate the salt 5, and elimination of a proton in 5 with Et,N the tetrathiafulvalene 6 with a 1,6-methano[ lO]annulene moiety. The spectroscopic and electrochemical properties of 6 are described, and also the syntheses and properties of' charge-transfer complexes 7 and 8, including the properties of electric conductivity of 7 and 8. The syntheses of 9-13 are reported and also their spectroscopic properties. Seit einigen Jahren beschiftigen wir uns rnit der Physik uind Chemie unkonventioneller Materialien [I]: mit Synthesen und mit den chemischen, physikalisch-chemischen, elektrischen Eigenschaften von Tetrathiafulvalenen mit 1,6-Methano[ 1 Olannulen-Partialstruktur [2--71 sowie rnit neuen S(lI),N-, S(IV),N-, Se(II),Nund Se(lV),N-Bindungssystemen. Im Hinblick auf eine mogliche neue Klasse von organischen elektrischen Leitern mit gerichteter Leitfiihigkeit berniihten wir uns um neue Molekulsysteme, ihre Charge-Transfer-Komplexe, Radikalsalze, ihre Bindungsverhaltnisse sowie ihre elektrischen Leitfiihigkeiten [8--221.

A star-shaped electron acceptor based on 5,5′-bibenzothiadiazole for solution processed solar cells

“…Toluene was distilled from sodium-benzophenone under nitrogen prior to use. 5,5 0 -Bibenzo[c][1,2,5]thiadiazole, 16 tributyl(4-dodecylthiophen-2-yl)stannane 17 and tris(4-(tributylstannyl)phenyl)amine 12c were synthesized according to the literature procedures.…”

Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

“…[68][69][70] The use of 2,1,3-benzoselenadiazoles in this way is described in detail in a review [71] which also contains a useful compilation of fully assigned 1 H, 13 C, and 77 Se data for such compounds. [82,83] Scheme 50 Reaction of 1,2-Diaminoarenes with Selenium Dioxide [82,83] [82] To a stirred soln of benzene-1,2-diamine (91; 50 g, 0.463 mol) in warm H 2 O (50 mL) was added a soln of SeO 2 (50 g, 0.45 mol) in warm H 2 O (50 mL). [73] A second major area of interest has been heterocyclic analogues of 2,1,3-benzoselenadiazoles and systems reported include 85 and 86, [74] 87 and 88, [75] and 89 and 90 (Scheme 49).…”

“…5,5¢-Bi-2,1,3-benzoselenadiazole (94): [83] To a stirred soln of biphenyl-3,3¢,4,4¢-tetramine (93; 428 mg, 2 mmol) in DMF at 100 8C was added all at once a soln of SeO 2 (444 mg, 4 mmol) in H 2 O (50 mL). After stirring at 100 8C for 3 min the mixture was allowed to cool and the precipitate was collected by filtration and washed with a little H 2 O. Recrystallization (1,2-dichlorobenzene) with charcoal treatment gave the product 94 as a yellow powder; yield: 713 mg (98%); mp 234 8C; sublimes above 130 8C.…”

A conjugated polymer based on 5,5′-bibenzo[c][1,2,5]thiadiazole for high-performance solar cells

“…5,5 0 -Bibenzo[c] [1,2,5]thiadiazole (BBT) was synthesized according to the literature. 18 The key monomer 4 was synthesized by treating BBT with HBr/Br 2 . Bromination of BBT gave a mixture of mono-, di-, tri-, and tetrabromide of BBT, which can be separated by column chromatography.…”

“…17 We are interested in 5,5 0 -bibenzo[c] [1,2,5]thiadiazole (BBT), which is a 5,5 0 -connected dimer of BT. There has been only one report 18 for BBT synthesis but no report regarding its use in the synthesis of organic semiconductors. Relative to BT, BBT has a stronger electron-accepting ability due to two BT units, facilitating the manipulation of the electronic structure (HOMO/ LUMO levels and band gap).…”