Synthesis and Electronic Properties of Oxidized Benzo[1,2-b:4,5-b′]dithiophenes

Abstract

Benzo[1,dithiophenes were oxidized under mild conditions with m-CPBA to yield the corresponding bis-sulfones (or tetraoxides). These sulfones possess redshifted absorption and emission spectra relative to the parent molecules. Electrochemical analyses reveal that the benzodithiophene molecules are transformed from electron donors to electron acceptors.

Solvent-Free Pd-Catalyzed Heteroaryl–Aryl Coupling via C–H Bond Activation for the Synthesis of Extended Heteroaromatic Conjugated Molecules

“…24 was prepared from 6 according to the literature. 16 Preparative column chromatography was carried out using Macherey-Nagel silica gel (60, particle size 0.063-0.2 mm).…”

“…To verify this hypothesis and further explore the suitability of our procedure, the electron-rich compound 6 was oxidized to the benzodithiophene-S,S-tetraoxide 8. 16 Despite being an electron-poor heterocyclic compound with promise for development of electron acceptor materials, 8 has been rarely used as building block for the synthesis of organic semiconductors. 17 To the best of our knowledge, only one example of regioselective direct arylation of benzodithiophene-S,S-tetraoxide has been reported so far, 18 based on the use of inexpensive Cu catalyst, but requiring anhydrous and inert conditions, toxic organic solvent (N,N-dimethylformamide) and large excess of aryl iodides (10 equiv).…”

Synthesis, characterization, and electronic properties of a thermally-labile isoindigo

“…Elemental analyses were performed by Atlantic Microlab, Inc., Norcross, GA. Thermogravimetric analyses were performed on a TA Instruments Q50 analyzer under a nitrogen atmosphere. Electrochemical measurements were performed with a Pine Research Instrumentation WaveNow USB potentiostat using methods previously described [11]. UV-vis spectra were recorded on an Ocean Optics USB HR4000 fiber optic spectrometer.…”

Benzodithiophene‐S,S‐tetraoxide (BDTT) as an Acceptor Towards Donor‐Acceptor (D‐A)‐Type Semiconducting Electropolymers

“…BDTT has seen limited utility as a building block for conjugated materials due to difficulties in chemical functionalization and low yields. [29,30] Despite its limited synthetic accessibility, BDTT was previously implemented in direct arylation studies for regioselective functionalization and proven as an efficient acceptor in D-A type molecular strategy for n-type materials. [30,31] Interestingly, its electrochemical synthesis and conductivity have not been studied.…”

“…Herein, we introduce benzodithiophene‐ S,S ‐tetraoxide (BDTT) as an acceptor for polymerization of p‐type materials for application in optoelectronic devices. BDTT has seen limited utility as a building block for conjugated materials due to difficulties in chemical functionalization and low yields [29,30] . Despite its limited synthetic accessibility, BDTT was previously implemented in direct arylation studies for regioselective functionalization and proven as an efficient acceptor in D‐A type molecular strategy for n‐type materials [30,31] .…”