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New Journal of Chemistry
DOI: 10.1039/C7NJ02735D
ARTICLE
Journal Name
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.35-1.00 (m, 80H), 0.80 (m, 24H), 0.63 (m, 16H). HR-MS (FD, [M] ):
Bunz, ACS Macro Lett. 2014,
3
, 415–418. g) C.-Y. Yu, S.-H. Yu,
+
S.-H. Wen, C.-C. Wang, Tetrahedron Lett. 2017, 58, 3854–
858.
168 2
calculated for [C124H O ] : m/z 1689.3039, found m/z 1689.3067.
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4
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a) A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B.
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Conclusions
Octaoctyl
substituted
prepared
fluorenophanetetraene
was
successfully
from octaoctyl substituted
tetrathia[3.3.3.3]fluorenophanes in three steps through
benzyne Stevens rearrangement, oxidation and thermal
a) T. Otsubo, V. Boekelheide, Tetrahedron Lett. 1975, 16
,
3
1
881–3884; b) C. A. Kingsbury, D. J. Cram, J. Am. Chem. Soc.
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elimination
reaction.
The
octaoctyl
substituted
fluorenophanetetraene was fully characterized by nuclear
magnetic resonance spectroscopy, high resolution mass
spectrometry and X-ray crystallography. The photooxidation
reaction of the fluorenophanetetraene was carried out in
dilute solution under UV light irradiation to give all trans linear
fluorenevinylene with aldehyde end groups. The optical
properties of fluorenophanetetraene and its linear compound
generated by photooxidation have been investigated and
compared. Theses cyclic conjugated molecules will be of
tremendous interest to those chemists and physicsts
interested in fluorescent devices, organic transistors and
organic photovoltaics in general. Thermal and photoinduced
Chem. 1975, 40, 2014–2016.
C.-Y. Yu, C.-H. Sie, C.-Y. Yang, New J. Chem. 2014, 38, 5003–
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8
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008.
C.-Y. Yu, M. Helliwell, J. Raftery, M. L. Turner, Chem. Eur. J.
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a) A. Cobas, E. Guitián, L. Castedo, J. Org. Chem. 1997, 62
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016, 14, 6079–6087.
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2
,
4
2
9
2
,
1
ring-opening
metathesis
polymerization
of
1
1
fluorenophanetetraene is currently under investigation.
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Acknowledgements
The authors thank the financial support from the National 12 F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G.
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Taiwan University of Science and Technology and the Ministry
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| J. Name., 2012, 00, 1-3
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