Compound 15

1-(4-(tert-Butyl)phenyl)-2-(4-methoxyphenyl)-3-phenyl-4-(4-(trifluoromethyl)phenyl)-9,10-dihydrotribenzo[a,c,e][8]annulene

From: Synthesis and characterization of hexaarylbenzenes with five or six different substituents enabled by programmed synthesis

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InChIKey ZMLSRIVYDXBLGE-UHFFFAOYSA-N

Compound data: CIF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

A 7-mL screw cap tube, containing a magnetic stirring bar, was flame-dried under vacuum and filled with nitrogen after cooling to room temperature. To this tube were added 6acdf (25.5 mg, 0.045 mmol, 1.0 equiv), dibenzo[a,e]cyclooctyne 14 (18.0 mg, 0.09 mmol, 2.0 equiv) and m-xylene (450 μL) under a stream of nitrogen. The flask was heated at 100 °C for 16 h. After cooling the reaction mixture to room temperature, the mixture was concentrated in vacuo, and the residue was purified by preparative thin-layer chromatography (hexane/CHCl3 = 2:1) to afford 15 (14.1 mg, 44% yield) as a white solid. 1H NMR (600 MHz, C2D2Cl4, 146 °C): δ 7.14 (d, J = 7.8 Hz, 2H), 7.06 (d, J = 7.8 Hz, 2H), 7.01–6.75 (m, 15H), 6.72–6.63 (m, 4H), 6.45 (d, J = 8.4 Hz, 2H), 3.62 (s, 3H), 3.35–3.23 (m, 2H), 3.03–2.94 (m, 2H), 1.17 (s, 9H); 13C NMR (150 MHz, C2D2Cl4, 146 °C): δ 157.4, 148.2, 144.6, 141.0, 140.9, 140.8, 140.7, 140.62, 140.59, 140.3, 140.2, 139.3, 139.0, 137.8, 137.2, 133.1, 132.3, 131.3, 130.9, 130.3, 130.2, 128.5, 128.3, 127.5 (q, 2JCF = 31.7 Hz), 126.4, 126.3, 126.0, 125.2, 124.6, 124.5, 124.1 (q, 1JCF = 274 Hz), 123.1, 123.0, 112.4, 55.1, 33.78, 33.75, 33.73, 30.9 (3JCF: not detected); HRMS (APCI) m/z calcd for C46H34F3O [M–C4H8]+: 659.25563, found 659.25314.

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