Table 2 The screening of reaction conditions with organic catalyst for the synthesis of ITIC with 2 equiv. IC group in toluenea.
From: Low-cost synthesis of small molecule acceptors makes polymer solar cells commercially viable
Entry | Catalyst | Catalyst (equivb) | T (°C) | Time (min) | Yieldc (%) |
|---|---|---|---|---|---|
1 | BF3 ∙ OEt2 | 5 | 0 | 60 | >99% |
2 | BF3 ∙ OEt2 | 5 | 28 | 15 | >99% |
3 | BF3 ∙ OEt2 | 1 | 28 | 30 | >99% |
4 | BF3 ∙ OEt2 | 2 | 28 | 20 | >99% |
5 | BF3 ∙ OEt2 | 8 | 28 | 10 | >99% |
6 | BF3 ∙ OEt2 | 10 | 28 | 5 | >99% |
7 | BF3 ∙ OEt2 | 1 | 60 | 10 | >99% |
8 | BF3 ∙ OEt2 | 2 | 60 | 8 | >99% |
9 | BF3 ∙ OEt2 | 5 | 60 | 5 | >99% |
10 | BF3 ∙ OEt2 | 8 | 60 | 5 | >99% |
11 | BF3 ∙ OEt2 | 10 | 60 | 5 | >99% |
12 | BF3 ∙ THF | 5 | 28 | 15 | >99% |
13 | BF3 ∙ HOAc | 5 | 28 | 15 | >99% |
14 | BF3 ∙ CH3CN | 5 | 28 | 15 | >99% |
15 | Cyanuric chloride | 10 | 60 | 60 | 0 |
16 | Carbon bromide | 10 | 60 | 60 | 0 |
17d | Pyridine | 15 | 60 | 720 | 22 |
18e | Pyridine | 15 | 60 | 360 | 83 |
