A kind of d-π-a-π-d type bodipy derivatives based on ethynyl bridge and preparation method thereof
An ethynyl and derivative technology, which is applied in the field of organic small molecule solar cell materials, can solve the problems of lack of sufficient molecular design and synthesis route optimization, low photovoltaic efficiency, single structure, etc., and achieves easy control of synthesis reaction conditions and wide ultraviolet absorption. Scope, effect of novel molecular structures
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Embodiment 1
[0095] Synthesis of target molecule BDP1
[0096] Add intermediate 3 (65mg, 0.1mmol), intermediate 4 (55mg, 0.25mmol), CuI (2mg, 0.01mmol), PdCl 2 (PPh 3 ) 2 (7mg, 0.01mmol), toluene (10mL) and triethylamine (10mL), vacuumize, pass through argon protection, and react with magnetic stirring at room temperature for 12h. Stop the reaction, extract with ethyl acetate, wash with saturated brine, and dry over anhydrous magnesium sulfate. Filtered, and the filtrate was rotovapped to remove the solvent. The crude product was purified by silica gel (200-300 mesh) column chromatography [eluent, V (petroleum ether): V (ethyl acetate) = 10:1] to obtain dark green solid BDP1 (59 mg), yield 71%. 1 H NMR (400MHz, CDCl 3 )δ:8.10(s,2H),7.70(dd,J=6.5,2.6Hz,4H),7.61–7.54(m,4H),7.48–7.42(m,4H),7.34(dd,J=6.0, 2.7Hz, 4H), 7.13(s, 2H), 7.06(d, J=8.7Hz, 2H), 4.07(t, J=6.5Hz, 2H), 1.89–1.83(m, 2H), 1.49(s, 12H), 1.31(d, J=6.6Hz, 10H), 0.88(d, J=3.6Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ:162.33,1...
Embodiment 2
[0098] Synthesis of target molecule BDP2
[0099] The synthesis method of BDP2 was similar to the synthesis method of BDP1. Intermediate 3 (65 mg, 0.1 mmol) and intermediate 5 (76 mg, 0.25 mmol) were used as substrates to obtain dark green solid BDP2 (68 mg) with a yield of 68%. 1 H NMR (400MHz, CDCl 3 )δ:8.13(s,2H),8.07(d,J=7.7Hz,2H),8.04(d,J=8.0Hz,2H),7.60(d,J=8.6Hz,2H),7.54(s, 2H), 7.46(d, J=7.2Hz, 2H), 7.40(d, J=8.2Hz, 2H), 7.35(d, J=8.0Hz, 2H), 7.22(d, J=7.3Hz, 2H) ,7.16(s,2H),7.07(d,J=8.7Hz,2H),4.28(t,J=7.2Hz,4H),4.08(t,J=6.5Hz,2H),1.92–1.83(m, 6H),1.36–1.24(m,30H),0.89–0.85(m,9H). 13 C NMR (101MHz, CDCl 3 )δ:162.31,146.11,141.18,140.00,134.83,132.69,132.20,126.25,125.68,123.10,122.48,122.33,120.61,120.34,119.49,119.18,115.07,114.84,113.20,111.81,108.87,94.01,81.57,68.50 ,43.22,31.85,31.82,29.73,29.40,29.27,29.20,29.15,28.98,27.33,26.06,22.70,22.63,14.14,14.09. 67 h 73 BF 2 N 4 O[M] + :998.585; found 998.294.
Embodiment 3
[0101] Synthesis of target molecule BDP3
[0102]The synthesis method of BDP3 is similar to the synthesis method of BDP1, using intermediate 3 (65mg, 0.1mmol) and intermediate 6 (124mg, 0.25mmol) as substrates, the dark green solid BDP2 (95mg) was purified with a yield of 69%. 1 H NMR (400MHz, CDCl 3 )δ: 8.03(s, 2H), 7.56(d, J=8.5Hz, 2H), 7.26(dd, J=8.5, 5.5Hz, 12H), 7.04(d, J=8.6Hz, 4H), 7.01( s,4H),6.99(s,4H),6.94(s,2H),6.92(s,2H),4.06(t,J=6.5Hz,2H),1.88–1.81(m,2H),1.71(s ,8H),1.36(m,34H),0.75(m,39H). 13 C NMR (101MHz, CDCl 3 )δ:162.32,148.41,146.00,145.48,144.20,132.61,132.27,127.12,125.74,125.71,124.39,121.23,114.78,114.51,93.03,81.01,68.45,57.17,38.26,32.44,31.84,31.75,31.44,29.72 , 29.34, 29.26, 29.14, 26.04, 22.69, 14.13. MALDI-TOF-MS, m / z: calcd for C 95 h 117 BF 2 N 4 O[M] + :1378.929; found 1378.320.
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