S-Alkylation of 1,3-dithiole-2-thiones

Heteroquinoid Merocyanine Dyes with High Thermal Stability as Absorber Materials in Vacuum‐Processed Organic Solar Cells

“…In addition to the Gompper reaction, we performed the following procedure. First, we carried out S‐alkylation of the donor unit, separately with trimethyl orthoformate and boron trifluoride diethyl etherate at mild conditions, to collect the air‐stable corresponding tetrafluoroborate salt at a high yield . Then, coupling with the heteroarylmalononitrile was carried out in formamide at 60 °C, yielding the desired dyes.…”

“…Materials: All chemical reagents (commercially available), unless otherwise specified, were used as received. The reagents 2‐bromo‐3,4‐dimethylthiophene, 2‐([2,2′‐bithiophen]‐5‐yl)malononitrile, 2‐methylthio‐1,3‐dithiolium tetrafluoroborate, 4,5‐bis(methylthio)‐2‐methylthio‐1,3‐dithiolium tetrafluoroborate and 2,6‐diphenylpyrylium tetrafluoroborate were prepared according to the literature.…”

Synthesis and characterization of new redox-active polymers based on 10-(1,3-dithiol-2-ylidene)anthracen-9(10H)-one derivatives

“…2,2 0 -Azobis(iso-butyronitrile) (AIBN) was recrystallized from methanol prior to use. 3-Bromoanthracen-9(10H)-one (1) [16] and 2-methyl-1,3-dithiolium tetrafluoroborate [17] were synthesized according to literature procedures. Unless otherwise noted, all reactions were performed under inert argon atmosphere.…”

Synthesis of 2-(Methylthio)-1,3-dithioles from 1,3-Dithiole-2-thiones: Important Building Blocks in Tetrathiafulvalene Chemistry

“…The methylation of 1,3-dithiole-2-thione can be performed with dimethylsulfate, methyl trifluoromethylsulfonate, or methyl fluorosulfonate (MFS), but all of these reagents are extremely toxic and generally hazardous to work with. We have therefore investigated a less hazardous method for the methylation and subsequent reduction.…”

“…Our work is inspired by a protocol reported by Neiland and co-workers . They developed a methylation protocol using a mixture of TMO, BF 3 ·Et 2 O and MFS (in a 1:1:1 ratio) to yield a wide range of 2-(methylthio)-1,3-dithiolium tetrafluoroborate salts.…”