10.1002/chem.201805975
Chemistry - A European Journal
(8R)-8,17-dihydro-8,17-methanobenzo[a]hexacen-19-one
(12)
funding from the EraNET Cofund Initiatives QuantERA under the
European Union's Horizon 2020 research and innovation
programme grant agreement ORQUID. This study has been
partially supported through the grant NEXT n° ANR-10-LABX-
0037 in the framework of the “Programme des Investissements
d’Avenir”.
In a well dried Schlenk flask the previous compound 11 (116 mg,
0.26 mmol) was dissolved in anhydrous dichloromethane (14
mL) under argon. Trimethylsilyl iodide (36 μL, 0.26 mmol, 1
equiv.) was added dropwise and the homogeneous reaction
mixture was stirred overnight at room temperature. Next day the
heterogeneous reaction mixture was heated at 45 °C for 3 h and
then cooled back to room temperature. The mixture was
concentrated in vacuo and diluted with hexane (2 mL), the
product was collected by filtration over a glass frit filter S4. The
product was washed with hexane and diethylether to afford pure
Keywords • Acenes • Heptacene • Dibenzopentacene •
Benzohexacene• Alternant hydrocarbons
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1
compound (100 mg, 96 %) as a white solid. H NMR (500 MHz,
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(2C), 126.66, 126.70 (2C), 127.18, 127.91 (2C), 128.55 (2C),
129.40, 129.86, 130.74 (2C), 131.16, 131.49 (2C), 131.81,
136.40, 136.49, 137.79, 137.97, 193.08 (C=O); CP MAS: 55.7
(bridgehead), 118.2-136.9 (aromatic), 191.7 (C=O); IR (CHCl3):
3045 w, 3013 w, 1933 w, 1785 s (C=O), 1626 w, 1567 w, 1542
w, 1518 w, 1491 w, 1470 w, 1447 m, 1419 m, 1355 w, 1339 w,
1288 w, 1237 w, 1179 w, 1165 w, 1141 m, 1033 w, 1001 w, 950
w, 907 s, 882 m, 815 m, 747 s, 681 w, 672 w, 654 w, 698 w, 554
w, 504 w, 470 m, 427 w cm‐1; DCI MS: ([378 - CO]+ ); HR DCI
MS: calcd for C30H18 378.1409 (M-CO); found 378.1306.
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Benzo[a]hexacene (5)
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an argon atmosphere for 15 minutes. CP MAS: 125.00; IR (KBr
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Acknowledgements
The authors thank Yannick Coppel (LCC-Toulouse) for recording
CP-MAS spectra, David Neumeyer (CEMES) for recording TGA
spectra, Christian Bourgerette (CEMES) and Isabelle Seguy
(LAAS) for help in spin-coating experiments. Jiří Rybáček (IOCB,
Prague) is gratefully acknowledged for the HPLC separation of
trans- and cis-DBPen 8a and 8b. Colin Martin (NAIST-CEMES)
is thanked for comments and corrections of the manuscript. A.J.
acknowledges funding from the Foundation EXPERIENTIA and
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from
ERDF/ESF
"UOCHB
MSCA
Mobility"
(No.
CZ.02.2.69/0.0/0.0/17_050/0008490). This research has been
funded in parts by the ICT-FET European Union Integrated
Project PAMS (Agreement No. 610446) and has received
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