Synthesis and photophysical properties of 9,10-Bis(3-aryl-2-naphthyl)anthracenes

Article abstract of DOI:10.1246/bcsj.20150341

The 9,10-bis(3-aryl-2-naphthyl)anthracenes 3 were prepared by the benzannulation reaction of 2-(phenylethynyl)benzaldehyde (1) and the corresponding 9,10-bis(arylethynyl)anthracenes 2 in the presence of Cu or Re catalyst and trichloroacetic acid. The photophysical properties of 3 in solutions were investigated.

Full text of DOI:10.1246/bcsj.20150341

Short Articles
(Scheme 1). We now plan to prepare the 9,10-bis(3-aryl-2-
naphthyl)anthracenes 3 as sterically hindered ADN derivatives
using this type of benzannulation reaction.12 In this paper, we
reported the synthesis, photophysical properties, and stability of 3.
The 9,10-bis(3-aryl-2-naphthyl)anthracenes 3 were prepared by
the Cu- or Re-catalyzed benzannulation reaction of 2-(phenyl-
ethynyl)benzaldehyde (1) and various 9,10-bis(arylethynyl)anthra-
cenes 2. These results are shown in Table 1. When 1 was allowed
to react with 9,10-bis(phenylethynyl)anthracene (2a) using Cu-
(OTf)2 or [ReCl(CO)5] and trichloroacetic acid in a 1,2-dichloro-
ethane solution at 80 °C, the corresponding ADN derivative 3a
was obtained in 59% and 36% yields, respectively (Entry 1). In
contrast, the yields of 3b and 3c by the use of the Re catalyst are
better than those of the Cu catalyst (Entries 2 and 3). In the case of
2d, the [ReCl(CO)5] catalyst led to the formation of 3d in moderate
yield, however, the Cu catalyst gave the no formation of 3d
(Entry 4).
In order to investigate the photophysical properties of ADN
derivatives 3, we measured the UV-vis and FL spectra of the ADN
derivatives 3 in dichloromethane solvent and their results are
shown in Figure 1 and Table 2 (see also, Supporting Information
(SI)). The absorbance maximum and the fluorescence wavelength
of 3 were similar to those of ADN. The FL spectra of 3 exhibited
vibrational fine structures due to their rigid planarity, although that
of ADN showed a broad peak. The fluorescence quantum yields of
3 were 0.36 to 0.50 and slightly decreased as compared to that of
ADN (0.54). A computational study of ADN and 3 was carried out
(Figure S1 in SI). The HOMO and LUMO orbitals of both ADN
and 3 were only delocalized in the anthracene ring. Moreover, the
values of HOMO and LUMO coefficients of 3 were quite similar
to those of ADN. Therefore, a significant effect of the substituents
on the aryl groups of 3 was not observed.
Synthesis and Photophysical
Properties of 9,10-Bis(3-aryl-
2-naphthyl)anthracenes
Rui Umeda,1 Masahiro Kimura,1
Yoshito Tobe,2
and Yutaka Nishiyama*1
Y. Nishiyama
1Faculty of Chemistry, Materials and
Bioengineering, Kansai University,
Suita, Osaka 564-8680
2Graduate School of Engineering Science,
Osaka University, Toyonaka, Osaka 560-8531
E-mail: nishiya@kansai-u.ac.jp
Received: October 1, 2015; Accepted: October 23, 2015;
Web Released: October 30, 2015
The 9,10-bis(3-aryl-2-naphthyl)anthracenes 3 were pre-
pared by the benzannulation reaction of 2-(phenylethynyl)benz-
aldehyde (1) and the corresponding 9,10-bis(arylethynyl)anthra-
cenes 2 in the presence of Cu or Re catalyst and trichloroacetic
acid. The photophysical properties of 3 in solutions were
investigated.
π-Conjugated organic compounds have recently become a
subject of intense research in material science. In particular, the
π-conjugated organic compounds are utilized as the organic light-
emitting diodes (OLEDs) in organic electronic devices due to
tuning of the color by molecular modification and low-cost
processability such as inkjet printing.1,2 Moreover, OLEDs can be
used for small and large flexible flat panel displays. Thus, various
types of π-conjugated compounds have already been synthesized
and applied to OLEDs.3 Anthracene is a promising candidate as
a blue OLED because of the wide energy band-gap, strong blue
fluorescence with high fluorescence quantum yield, and easy modi-
fication. Indeed, anthracene4 and its derivatives5 have been inten-
sively studied in order to develop novel and efficient blue OLEDs.
Among them, 9,10-di(2-naphthyl)anthracene (ADN) (Chart 1) and
its derivatives are well-known blue fluorescent dyes for application
in OLEDs.6-9
We next performed the stability experiment in room light. Dilute
solutions (ca. 10¹5 M) of 3 and ADN in non degassed dichloro-
methane were monitored by UV-vis spectroscopy and stored in
cat.Cu, CF2HCOOH
O
or
R1
R2
cat.Re, CCl3COOH
R1
H
+
R2
Scheme 1.
Table 1. Cu- or Re-catalyzed benzannulation of 1 and 2
cat.Cu(OTf)2 (16 mol%)
Ar
O
or
cat.ReCl(CO)5 (16 mol%)
H
Recently, the selective syntheses of 2,3-disubstituted naphtha-
lenes by the Cu- or Re-catalyzed benzannulation reaction of 2-
(phenylethynyl)benzaldehyde and alkynes in the presence of the
carboxylic acid, CF2HCOOH and CCl3COOH, as proton source
were reported by Asao and Yamamoto10 and our11 groups
+
3
CCl3COOH (3.0 equiv)
ClCH2CH2Cl, 80 °C
Ar
(3.0 equiv)
(1.0 equiv)
1
2
3, Yield/%a)
Ar
Entry
Ar
a, Ph
b, 4-MeOC6H4
c, 3,5-di-t-BuC6H3
cat. Cu
cat. Re
1
2
3
4
59
10
28
36
32
52
54
Ar
ADN
3
d, 3,5-di-t-Bu-4-MeOC6H2
N.D.
Chart 1.
a) Isolated yields based on 2.
110 | Bull. Chem. Soc. Jpn. 2016, 89, 110–112 | doi:10.1246/bcsj.20150341
© 2016 The Chemical Society of Japan

spectrometer. Fluorescence spectra were measured on a HITACHI
F-7000 spectrometer. Absolute quantum yield was measured using
an integrating sphere. All solutions for UV-vis absorption and
fluorescence spectral measurements were prepared in spectrograde
solvent.
General Procedure for Synthesis of 9,10-Bis(arylethynyl)-
anthracenes 2 (GP1). A solution of the corresponding terminal
alkyne (3 equiv), 9,10-dibromoanthracene (1.0 equiv), [Pd(PPh3)4]
(10-14 mol %), and CuI (24-29 mol %) in degassed diisopropyl-
amine (10 mL) and degassed THF (20 mL) was stirred at 80 °C
for 20 h under a nitrogen atmosphere. The reaction mixture was
diluted with CHCl3 and washed with saturated NaHCO3 aq. and
brine. The organic layer was dried over MgSO4. After removal
of the solvent under reduced pressure, the residue was purified
by chromatography on SiO2 to give the crude product. Further
purification was carried out by recyclable preparative HPLC.
2a (Ar = Ph)13 was obtained using phenylacetylene (4.53 mmol,
463 mg), 9,10-dibromoanthracene (1.50 mmol, 504 mg), [Pd-
(PPh3)4] (0.205 mmol, 238 mg), and CuI (0.43 mmol, 82 mg) by
Figure 1. UV-vis absorption and fluorescence spectra of ADN
and 3a in CH2Cl2.
Table 2. Optical properties of ADN and 3a-3da)
1
¹1
-
abs/nm (©103 ¾/M¹1 cm
)
-
em/nm
Φfb)
applying GP1; H NMR (400 MHz, CDCl3): ¤ 8.72-8.68 (m, 4H),
7.80-7.77 (m, 4H), 7.67-7.63 (m, 4H), 7.49-7.41 (m, 6H).
13C NMR (100 MHz, CDCl3): ¤ 132.08, 131.68, 128.69, 128.56,
127.24, 126.81, 123.41, 118.45, 102.39, 86.47.
ADN
3a
3b
3c
3d
358 (8.4), 376 (13.5), 397 (12.7)
361 (7.8), 380 (12.8), 402 (12.2)
362 (8.5), 381 (14.3), 403 (13.7)
366 (7.1), 378 (18.3), 399 (18.0)
359 (11.2), 377 (18.3), 400 (19.1)
427
0.54
0.36
0.50
0.37
0.39
421, 441
420, 440
432
2b (Ar = 4-MeOC6H4)14 was obtained using 4-ethynylanisole
(4.39 mmol, 580 mg), 9,10-dibromoanthracene (1.60 mmol, 538
mg), [Pd(PPh3)4] (0.202 mmol, 233 mg), and CuI (0.40 mmol, 76
433
a) ADN (c = 2.21 © 10¹5 M), 3a (c = 2.40 © 10¹5 M), 3b (c =
1.00 © 10¹5 M), 3c (c = 2.28 © 10¹5 M), 3d (c = 2.12 © 10¹5 M).
b) Absolute quantum yield measured using an integrating sphere.
1
mg) by applying GP1; H NMR (400 MHz, CDCl3): ¤ 8.68 (dd,
J = 6.8, 3.2 Hz, 4H), 7.73-7.71 (m, 4H), 7.63 (dd, J = 6.6, 3.4 Hz,
4H), 6.98 (d, J = 8.8 Hz, 4H), 3.89 (s, 6H). 13C NMR (100 MHz,
CDCl3): ¤ 159.96, 133.16, 131.95, 127.29, 126.61, 118.43, 115.59,
114.20, 102.42, 85.36, 55.40.
volumetric flasks at ambient temperature on the working bench.
The results of the UV-vis spectra of 3 and ADN are shown in
Figures S4-S7. The intensity of the absorption peaks correspond-
ing to the anthracene framework (around 380 nm) in UV-vis
spectra of ADN clearly decreased over time. On the other hand,
in the case of 3, the intensity of the absorption peaks did not
remarkably change for nearly 2 months. These results indicated
that 3 was much more light- and air-stable than ADN.
In conclusion, the 9,10-bis(3-aryl-2-naphthyl)anthracenes 3
were prepared by the benzannulation reaction of 2-(phenyl-
ethynyl)benzaldehyde (1) and the corresponding 9,10-bis(aryl-
ethynyl)anthracenes 2 in the presence of Cu(OTf)2 or [ReCl(CO)5]
complexes as catalysts and trichloroacetic acid as proton source.
The photophysical properties of 3 in solution are similar to those of
ADN. Based on the stability experiment, the aryl-substituted ADN
derivatives 3 were much more stable than ADN. These results
clearly show that the sterically hindered ADN derivatives 3 are
very hopeful candidates for blue fluorescent dyes for application in
OLEDs and studies in this area are currently in progress.
2c (Ar = 3,5-di-t-BuC6H3) was obtained using 1,3-di-tert-butyl-
5-ethynylbenzene (3.28 mmol, 703 mg), 9,10-dibromoanthracene
(1.10 mmol, 370 mg), [Pd(PPh3)4] (0.112 mmol, 129 mg), and CuI
(0.26 mmol, 50 mg) by applying GP1; mp >300 °C. 1H NMR
(400 MHz, CDCl3): ¤ 8.74-8.72 (m, 4H), 7.67-7.65 (m, 4H), 7.61
(s, 4H), 7.51 (s, 2H), 1.41 (s, 36H). 13C NMR (100 MHz, CDCl3):
¤ 151.12, 132.15, 127.37, 126.71, 125.91, 123.30, 122.42, 118.55,
103.43, 85.13, 34.93, 31.41. IR (KBr): 3072, 3056, 2963, 2902,
2867, 2197, 1589, 1449, 1435, 1391, 1362, 1247, 1219, 1202,
1092, 873, 765, 701 cm¹1. MS (FAB): 603 (M + H+). HRMS (EI):
calcd for C46H50: 602.3913. found 602.3918.
2d (Ar = 3,5-di-t-Bu-4-MeOC6H2) was obtained using 1,3-di-
tert-butyl-5-ethynyl-2-methoxybenzene (2.93 mmol, 716 mg),
9,10-dibromoanthracene (1.11 mmol, 373 mg), [Pd(PPh3)4] (0.114
mmol, 132 mg), and CuI (0.24 mmol, 50 mg) by applying GP1; mp
1
>300 °C. H NMR (400 MHz, CDCl3): ¤ 8.72-8.69 (m, 4H), 7.65
(s, 4H), 7.65-7.63 (m, 4H), 3.76 (s, 6H), 1.51 (s, 36H). 13C NMR
(100 MHz, CDCl3): ¤ 160.54, 144.34, 132.10, 130.14, 127.36,
126.64, 118.53, 117.75, 103.11, 84.95, 64.47, 35.85, 32.01. IR
(KBr): 3059, 2958, 2870, 2201, 1421, 1390, 1362, 1256, 1223,
1116, 1053, 1011, 888, 767, 693 cm¹1. MS (FAB): 663 (M + H+).
HRMS (EI): calcd for C48H5O2: 662.4124. found 662.4114.
General Procedure for Synthesis of 9,10-Bis(3-aryl-2-naph-
thyl)anthracenes 3 (GP2). A solution of 2-(phenylethynyl)benz-
aldehyde (1) (3 equiv), 9,10-bis(arylethynyl)anthracene 2 (1 equiv),
trichloroacetic acid (3 equiv), and Cu(OTf)2 or [ReCl(CO)5] (16
mol %) in ClCH2CH2Cl (5 mL) was heated at 80 °C for 20 h under
a nitrogen atmosphere. The reaction mixture was diluted with
CHCl3 and washed with saturated NaHCO3 aq. and brine. The
organic layer was dried over MgSO4. After removal of the solvent
Experimental
General. FT-IR spectra were recorded on a JASCO FT/IR-
4100 instrument. H NMR spectra were recorded at 400 MHz and
1
13C NMR spectra at 100 MHz on JEOL a JNM-ECS-400 or a JEOL
JNM-AL400. Chemical shifts were reported in ppm relative to
tetramethylsilane or residual solvent as the internal standard. Mass
spectral analyses were performed on a JEOL JMS-700 spectrom-
eter for EI and FAB ionization. Preparative HPLC separation was
undertaken with a JAI LC-908 chromatograph using 600 mm © 20
mm JAIGEL-1H and 2H GPC columns with CHCl3 as an eluent.
UV-vis absorption spectra were recorded on a HITACHI U-2910
Bull. Chem. Soc. Jpn. 2016, 89, 110–112 | doi:10.1246/bcsj.20150341
© 2016 The Chemical Society of Japan | 111

under reduced pressure, the residue was purified by chromatog-
raphy on SiO2 to give the crude product. Further purification was
carried out by recyclable preparative HPLC.
versities, and the Kansai University Research Grants: Grant-in-Aid
for Encouragement of Scientists.
Supporting Information
3a (Ar = Ph) was obtained using 1 (0.902 mmol, 0.186 g), 2a
(0.299 mmol, 0.113 g), [ReCl(CO)5] or Cu(OTf)2 (16 mol %), and
CCl3COOH (0.930 mmol, 0.152 g) by applying GP2 as a yellow
Computational study and UV-vis absorption and fluorescence
spectra of ADN derivatives and 1H and 13C NMR spectra of 2a-2d
and 3a-3d. This material is available on http://dx.doi.org/10.1246/
bcsj.20150341.
1
solid; mp >300 °C. H NMR (400 MHz, CDCl3): ¤ 8.07 (s, 2H),
8.02 (d, J = 8.0 Hz, 2H), 7.89 (s, 1H), 7.86 (d, J = 7.2 Hz, 2H),
7.63-7.53 (m, 8H), 7.21-7.16 (m, 4H), 7.07-6.88 (m, 6H), 6.83 (dd,
J = 7.6, 3.6 Hz, 3H). 13C NMR (100 MHz, CDCl3): ¤ 141.60,
140.92, 136.15, 135.85, 133.21, 132.49, 131.62, 130.17, 128.95,
128.51, 127.88, 127.71, 127.57, 127.06, 126.47, 126.33, 126.26,
124.92. IR (KBr): 3053, 3023, 1488, 1440, 1379, 1213, 1075, 1029,
894, 758, 698 cm¹1. MS (EI): 582 (M+). HRMS (EI): calcd for
C46H30: 582.2348. found 582.2342.
References
1
2
H. Sirringhaus, Adv. Mater. 2014, 26, 1319.
X.-H. Zhu, J. Peng, Y. Cao, J. Roncali, Chem. Soc. Rev. 2011,
40, 3509.
3
Fore a recent review, see: Z. Ma, P. Sonar, Z.-K. Chen, Curr.
Org. Chem. 2010, 14, 2034.
3b (Ar = 4-MeOC6H4) was obtained using 1 (0.931 mmol,
0.192 g), 2b (0.308 mmol, 0.135 g), [ReCl(CO)5] or Cu(OTf)2 (16
mol %), and CCl3COOH (0.943 mmol, 0.154 g) by applying GP2
as a yellow solid; mp >300 °C. 1H NMR (400 MHz, CDCl3):
¤ 8.08 (s, 2H), 8.03 (d, J = 8.4 Hz, 2H), 7.87 (s, 2H), 7.84 (d,
J = 8.4 Hz, 2H), 7.66-7.52 (m, 8H), 7.23-7.18 (m, 4H), 7.01 and
6.45 (AA¤BB¤, JAB = 9.0 Hz, 8H), 3.69 (s, 6H). 13C NMR (100
MHz, CDCl3): ¤ 158.22, 140.98, 136.35, 135.90, 133.49, 133.30,
132.31, 131.82, 130.22, 129.72, 128.79, 127.79, 127.66, 127.10,
126.40, 126.13, 124.97, 113.11, 54.95. IR (KBr): 3033, 2924,
2852, 1517, 1247, 1180, 1033, 827 cm¹1. MS (EI): 643 (M+).
HRMS (EI): calcd for C48H34O2: 642.2559. found 642.2538.
3c (Ar = 3,5-di-t-BuC6H3) was obtained using 1 (0.824 mmol,
0.170 g), 2c (0.219 mmol, 0.132 g), [ReCl(CO)5] or Cu(OTf)2 (16
mol %), and CCl3COOH (0.747 mmol, 0.122 g) by applying GP2
4
5
W. Helfrich, W. G. Schneider, Phys. Rev. Lett. 1965, 14, 229.
For recent selected reports, see: a) L. Li, B. Jiao, Y. Yu, L.
Ma, X. Hou, Z. Wu, RSC Adv. 2015, 5, 59027. b) H. Park, J. Lee, H.
Kang, H. Y. Chu, J.-I. Lee, S.-K. Kwon, Y.-H. Kim, J. Mater. Chem.
2012, 22, 2695. c) I. Cho, S. H. Kim, J. H. Kim, S. Park, S. Y. Park,
J. Mater. Chem. 2012, 22, 123. d) A. Thangthong, D. Meunmart,
N. Prachumrak, S. Jungsuttiwong, T. Keawin, T. Sudyoadsuk, V.
Promarak, Tetrahedron 2012, 68, 1853. e) J.-J. Oh, Y.-J. Pu, H. Sasabe,
K. Nakayama, J. Kido, Chem. Lett. 2011, 40, 1092. f) K.-R. Wee,
W.-S. Han, J.-E. Kim, A.-L. Kim, S. Kwon, S. O. Kang, J. Mater.
Chem. 2011, 21, 1115. g) J. Wang, W. Wan, H. Jiang, Y. Gao, X. Jiang,
H. Lin, W. Zhao, J. Hao, Org. Lett. 2010, 12, 3874. h) S. Tao, Y. Zhou,
C.-S. Lee, S.-T. Lee, D. Huang, X. Zhang, J. Phys. Chem. C 2008, 112,
14603. i) T. Karatsu, R. Hazuku, M. Asuke, A. Nishigaki, S. Yagai, Y.
Suzuri, Org. Electron. 2007, 8, 357. j) A. K. Tripathi, M. Heinrich, T.
Siegrist, J. Pflaum, Adv. Mater. 2007, 19, 2097. k) P. Raghunath, M. A.
Reddy, C. Gouri, K. Bhanuprakash, V. J. Rao, J. Phys. Chem. A 2006,
110, 1152.
1
as a yellow solid; mp >300 °C. H NMR (400 MHz, CDCl3): ¤
8.07 (s, 2H), 8.05 (d, J = 10.8 Hz, 1H), 7.82 (d, J = 8.4 Hz, 2H),
7.77 (s, 2H), 7.71-7.69 (m, 4H), 7.56 (dd, J = 7.4, 7.2 Hz, 2H),
7.53 (dd, J = 7.4, 7.2 Hz, 2H), 7.29-7.27 (m, 2H), 7.21 (s, 4H),
6.96 (s, 2H), 0.84 (s, 36H). 13C NMR (100 MHz, CDCl3): ¤
149.27, 142.60, 140.31, 136.76, 136.38, 133.08, 132.33, 131.78,
130.74, 129.22, 127.74, 127.61, 127.53, 126.33, 126.07, 124.68,
123.80, 119.65, 34.39, 30.97. IR (KBr): 3056, 2962, 2902, 2867,
1593, 1475, 1439, 1362, 1247, 1158, 1139, 1025, 938, 906, 890,
872, 767, 748, 714 cm¹1. MS (FAB): 807 (M + H+). HRMS (EI):
calcd for C62H62: 806.4852. found 806.4881.
6
7
J. M. Shi, C. H. Chen, K. P. Klubek, US Patent 5974247, 2000.
Y. Q. Li, M. K. Fung, Z. Xie, S.-T. Lee, L.-S. Hung, J. Shi,
Adv. Mater. 2002, 14, 1317.
8
9
J. Shi, C. W. Tang, Appl. Phys. Lett. 2002, 80, 3201.
For recent selected reports, see: a) H. Chen, W. Liang, Y. Chen,
G. Tian, Q. Dong, J. Huang, J. Su, RSC Adv. 2015, 5, 70211. b) G. H.
Kim, R. Lampande, J. H. Kong, J. M. Lee, J. H. Kwon,
J. K. Lee, J. H. Park, RSC Adv. 2015, 5, 31282. c) C.-L. Wu, C.-H.
Chang, Y.-T. Chang, C.-T. Chen, C.-T. Chen, C.-J. Su, J. Mater. Chem.
C 2014, 2, 7188. d) S. Tao, S. Xu, X. Zhang, Chem. Phys. Lett. 2006,
429, 622. e) M.-T. Lee, C.-H. Liao, C.-H. Tsai, C.-H. Chen, Adv.
Mater. 2005, 17, 2493. f) M.-T. Lee, H.-H. Chen, C.-H. Liao, C.-H.
Tsai, C. H. Chen, Appl. Phys. Lett. 2004, 85, 3301.
3d (Ar = 3,5-di-t-Bu-4-MeOC6H2) was obtained using 1 (0.766
mmol, 0.158 g), 2d (0.216 mmol, 0.143 g), [ReCl(CO)5] (16
mol %), and CCl3COOH (0.845 mmol, 0.138 g) by applying GP2
1
as a yellow solid; mp >300 °C. H NMR (400 MHz, CDCl3): ¤
10 a) N. Asao, Synlett 2006, 1645. b) N. Asao, T. Nogami, S. Lee,
Y. Yamamoto, J. Am. Chem. Soc. 2003, 125, 10921. c) N. Asao, K.
Takahashi, S. Lee, T. Kasahara, Y. Yamamoto, J. Am. Chem. Soc.
2002, 124, 12650.
11 a) R. Umeda, K. Kaiba, S. Morishita, Y. Nishiyama,
ChemCatChem 2011, 3, 1743. b) R. Umeda, H. Tabata, Y. Tobe, Y.
Nishiyama, Chem. Lett. 2014, 43, 883.
12 The synthesis of 3a by iron-catalyzed benzannulation reaction
of 2-alkylbenzaldehyde and 2a was reported, see: S. Zhu, Y. Xiao, Z.
Guo, H. Jiang, Org. Lett. 2013, 15, 898.
13 a) A. Fürstner, G. Seidel, Tetrahedron 1995, 51, 11165.
b) D. Kang, D. Eom, H. Kim, P. H. Lee, Eur. J. Org. Chem. 2010,
2330.
8.00 (d, J = 8.4 Hz, 2H), 7.94 (s, 2H), 7.78 (d, J = 8.0 Hz, 2H),
7.72 (s, 2H), 7.67 (dd, J = 6.8, 3.2 Hz, 4H), 7.56 (dd, J = 7.4,
1.2 Hz, 2H), 7.50 (dd, J = 8.0, 2.8 Hz, 2H), 7.26-7.23 (m, 6H),
7.16 (s, 4H), 3.50 (s, 6H), 0.90 (s, 36H). 13C NMR (100 MHz,
CDCl3): ¤ 157.99, 142.26, 142.10, 136.80, 136.29, 135.53, 133.08,
132.24, 131.77, 130.80, 129.31, 127.75, 127.65, 127.59, 127.51,
126.30, 126.00, 124.85, 63.73, 35.36, 31.93. IR (KBr): 3056,
3008, 2960, 2868, 2363, 1449, 1413, 1395, 1362, 1260, 1224,
1116, 1013, 883, 766, 746, 696 cm¹1. MS (FAB): 867 (M + H+).
HRMS (EI): calcd for C64H66O2: 866.5063. found 866.5038.
This work was financially supported by the Grant-in-Aid for
Scientific Research on Innovative Areas, the MEXT-Supported
Program for the Strategic Research Foundation at Private Uni-
14 C. V. Suneesh, K. R. Gopidas, J. Phys. Chem. C 2009, 113,
1606.
112 | Bull. Chem. Soc. Jpn. 2016, 89, 110–112 | doi:10.1246/bcsj.20150341
© 2016 The Chemical Society of Japan