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K. P. U. Perera et al. / Tetrahedron 58 (2002) 10197–10203
88.06, 88.89, 90.89, 91.06, 122.74, 122.78, 125.64, 126.44,
127.25, 127.29, 128.09, 128.22, 129.44, 131.24, 132.51,
132.66, 132.72. HRMS for C39H18F6S calcd (found):
728.0195 (728.0193).
orange solid in 68% yield, mp 152–1578C. FTIR (KBr
disk): (cm21) 683, 741, 780, 820, 835, 911, 1020, 1100,
1211, 1250, 1300, 1400, 1460, 1470, 1581, 2215, 2954. 1H
NMR (300 MHz, CDCl3) d: 7.24–7.29 (m, 4H), 7.61–7.75
(m, 12H), 7.94 (m, 2H), 8.65–8.67 (m, 4H). 13C NMR
(500 MHz, CDCl3) d: 87.45, 87.55, 93.32, 94.10, 123.06,
123.11, 124.94, 126.23, 127.24, 127.78, 127.90, 130.79,
132.99, 136.23, 139.65, 143.39, 143.45, 150.17, 150.21.
HRMS for C40H22N4 calcd (found): 558.1844 (558.1848).
4.5.8. 2,2-Bis(3,4-di(2-2-ethynylpyridyl)-1,1,1,3,3,3-
hexafluoropropane (4b). The crude product was purified
by column chromatography (silica gel, 1:1 hexane/ethyl
acetate) and gave 3.45 g of an orange solid in 75% yield, mp
215–2168C. FTIR (KBr disk): (cm21) 713, 736, 785, 831,
881, 968, 987, 1044, 1079, 1110, 1151, 1185, 1204, 1254,
1372, 1422, 1456, 1486, 1570, 1582, 1723, 2214, 2919. 1H
NMR (300 MHz, CDCl3) d: 7.26–7.28 (m, 3H), 7.38–7.41
(m, 2H), 7.68–7.74 (m, 13H), 8.62–8.66 (m, 4H). 13C NMR
(500 MHz, CDCl3) d: 64.00 (m), 87.18, 87.37, 93.51, 94.07,
123.39, 123.48, 125.86, 126.55, 128.02, 128.23, 130.34,
132.40, 133.46, 133.80, 136.60, 136.85, 142.59, 142.74,
149.72, 149.93. HRMS C43H22N4F6 calcd (found):
708.1748 (708.1752).
Acknowledgements
We are grateful to the National Science Foundation
(CAREER Award DMR-9985160), The Army Research
Office, (DAAD19-00-1-0114) and South Carolina EPSCoR
for financial support and Mettler-Toledo for the donation of
a DSC820 system to Clemson University. We also thank
Y. P. Sun and Jayasundara Bandara (Clemson University)
for help with emission data and Lane Coffee, Jr. and Chris
Topping (Clemson University) for valuable discussions and
help. DWS is a Cottrell Scholar of Research Corporation.
4.5.9. 3,30,4,40-Tetra(2-ethynylthienyl)phenyl ether (4c).
The crude product was purified by column chromatography
(silica gel, 10:1 hexane/ethyl acetate) and gave 3.40 g of an
orange solid 70% yield, mp 210–2118C. FTIR (KBr disk):
(cm21) 592, 689, 837, 964, 1040, 1198, 1351, 1417, 1468,
1524, 1590, 2195, 2938, 3086. 1H NMR (300 MHz, CDCl3)
d: 6.97–7.03 (m, 6H), 7.14–7.15 (m, 2H), 7.29–7.34 (m,
8H), 7.50–7.53 (d, J¼8.5 Hz, 2H). 13C NMR (300 MHz,
CDCl3) d: 86.70, 87.95, 91.26, 91.37, 119.38, 120.00,
121.42, 123.00, 123.50, 127.28, 127.31, 127.65, 128.12,
132.14, 132.65, 133.27, 156.19. HRMS for C36H18O1S4
calcd (found): 594.0240 (594.0231).
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