Metal-free organic dyes with benzothiadiazole as an internal acceptor for dye-sensitized solar cells

Organic sensitizers possessing carbazole donor and indeno[1,2-b] thiophene spacer for efficient dye sensitized solar cells

“…[21,22] In addition, the absorption patterns of all dyes are very similar, as shown in Figure 1 Details of photo-physical properties for all dyes are summarized in Table 1.…”

“…carbaldehyde (3) [22] : 3,6-bis(4-(hexyloxy)phenyl)-9H-carbazole (0.69 g, 1.33 mmol), 5'-(4-bromophenyl)-2,2'-bithiophene-5-carbaldehyde (0.56 g, 1.60 mmol), Pd 2 (dba) 3 found, 854.33.…”

Boron–dibenzopyrromethene-based organic dyes for application in dye-sensitized solar cells

“…4) was prepared from 4-bromo-2-hydroxyacetophenone through 4 steps. 12 2-(5-(5,5-Dimethyl-1,3-dioxan-2-yl)-3-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5) was also prepared from 2-bromo-3-hexyl-5-formylthiophene 13 through protection of aldehyde using neopentyl glycol, followed by borylation with 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane in the presence of n-BuLi; 1 H NMR of 5 (300 MHz, CDCl 3 ) d (ppm) 0.78 (s, 3H), 0.87 (t, 3H, J ¼ 6.40 Hz), 1.25 (s, 3H), 1.25-1.36 (m, 18H), 1.50-1.59 (m, 2H), 2.81 (t, 2H, J ¼ 7.62 Hz), 3.61 (d,2H,J ¼ 10.89 Hz),3.73 (d,2H,J ¼ 11.01 Hz),5.59 (s,1H),7.04 (s,1H), FAB MS: m/z 407 [M À 1] + , 408 [M] + . Details of synthetic procedures for the intermediate compounds 6-14 are described in the ESI.…”

“…For 1; 1 H NMR (500 MHz, DMSO-d 6 ) d (ppm) 0.79 (t, 6H, J ¼ 6.77 Hz), 1. 14-1.20 (m, 12H), 1.48-1.59 (m, 4H), 2.62-2.66 (m, 4H), 3.69 (s, 3H), 3.76 (s, 3H), 7.03 (t, 1H, J ¼ 7.53 Hz), 7.10 (t, 1H, J ¼ 7.47 Hz), 7.20 (d,1H,J ¼ 8.30 Hz),7.24 (d,1H,J ¼ 8.45 Hz),7.37 (s,1H),7.39 (s,1H),7.45 (d,1H,J ¼ 7.50 Hz),7.51 (t,3H,J ¼ 8.18 Hz),7.71 (d,2H,J ¼ 8.45 Hz),7.94 (s,2H),8.30 (d,1H,J ¼ 8.30),8.31 (d,1H,J ¼ 8.20 Hz),8.43 (s,2H),8.84 and 8.85 (s,1H), 13.75 (broad signal, 2H); 13 C NMR (125 MHz, DMSO-d 6 ) d (ppm): 163.5,157.3,157.2,150.0,149.8,148.8,147.0,146.4,142.4,140.2,133.5,132.9,132.8,132.0,131.7,131.6,131.3,130.3,130.2,129.9,129.4,127.2,127.1,…”

“…For 3; 1 H NMR (500 MHz, DMSO-d 6 ) d (ppm) 0.79 (t, 6H, J ¼ 6.90 Hz), 1. 14-1.19 (m, 12H), 1.48-1.59 (m, 4H), 2.61-2.66 (m, 4H), 3.69 (s, 3H), 3.75 and 3.76 (s, 3H), 7.03 (t, 1H, J ¼ 7.45 Hz), 7.10 (t, 1H, J ¼ 7.53 Hz), 7.19 (d,0.5H,J ¼ 8.70 Hz),7.20 (d,0.5H, J ¼ 8.25 Hz), 7.23 (d, 0.5H, J ¼ 8.70 Hz), 7.23 (d,0.5H,J ¼ 8.40 Hz),2H), 7.44 (t, 1H, J ¼ 6.05 Hz), 7.49-7.52 (m, 3H), 7.68-7.72 (m, 2H), 7.90 (s, 1H), 7.97 and 7.98 (s, 1H), 8.29 (d,1H,J ¼ 8.35 Hz) , 8.30 (d, 1H, J ¼ 8.45 Hz), 8.38 (s, 1H), 8.83 and 8.84 (s, 1H), 9.87 Fig. 1 Chemical structures of dyes 1, 2 and 3. (s, 1H), 13.77 (broad signal, 1H); 13 C NMR (125 MHz, DMSO-d 6 ) d (ppm): 183.9, 163.…”