Abstract
Stille coupling of 5-chloro-4-oxo-4H-1,2,6-thiadiazin-3-yl trifluoromethanesulfonate (7) with tributyl(3-n-hexylthien-2-yl)stannane and Pd(Ph3P)2Cl2 in PhMe at ca. 20 °C, for 24 h gave 3-chloro-5-(3-n-hexylthien-2-yl)-4H-1,2,6-thiadiazin-4-one (9) with a 60% yield. The latter is a potentially useful building block for the synthesis of oligomeric and polymeric donors for organic photovoltaics.
Highlights
Non-oxidized 4H-1,2,6-thiadiazines are a rare class of heterocycles
4H-1,2,6-thiadiazines were characterized by resonance Raman (RR), absorption (UV–vis), and photoluminescence (PL) spectroscopies to better understand their optical properties [14], while an electrochemical study of selected 1,2,6-thiadiazines [15] revealed that they might have useful electronic properties
PC70 BM were used in bulk heterojunction (BHJ) solar cells with Power Conversion Efficiencies (PCE) of ~2.8%, while in a later work, 4H-1,2,6-thiadiazine-containing polymers showed PCEs of up to 3.8% [17]
Summary
Non-oxidized 4H-1,2,6-thiadiazines are a rare class of heterocycles. recent interest in their properties and applications has fueled the development of their chemistry: many. 4H-1,2,6-thiadiazines were characterized by resonance Raman (RR), absorption (UV–vis), and photoluminescence (PL) spectroscopies to better understand their optical properties [14], while an electrochemical study of selected 1,2,6-thiadiazines [15] revealed that they might have useful electronic properties. We recently prepared a series of small-molecule non-S-oxidized 4H-1,2,6-thiadiazin-4-ones. 2–6 from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (1) and investigated them as efficient electron donors in solution-processed bulk heterojunction (BHJ) solar cells as substitutes to the widely used. PC70 BM were used in BHJ solar cells with Power Conversion Efficiencies (PCE) of ~2.8%, while in a later work, 4H-1,2,6-thiadiazine-containing polymers showed PCEs of up to 3.8% [17]
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