10.1002/asia.201801339
Chemistry - An Asian Journal
FULL PAPER
6-311g* basis set for Se only and 6-31g* basis set for all other atoms). All
calculations were performed with the gas phase.
Prof. H. S. Park acknowledges support from by a grant from Samsung
Science & Technology Foundation (SSTF-BA1702-09). The Molecular
Logic Gate Laboratory operated by Prof. D. G. Churchill acknowledges
support from the Mid-Career Researcher Program through the NRF
(National Research Foundation) of Korea (NRF-2014R1A2A1A11052980)
funded by the MEST. Tesla Yudhistira (LPDP/201412022313)
acknowledges Lembaga Pengelola Dana Pendidikan (LPDP) Indonesia
Endowment Fund for the fellowship and KAIST for providing research
facilities. Dr. Mahesh B. Halle acknowledges the BK21plus research
fellowship and KAIST for providing research facilities. The research
support staff at KAIST facilitated the acquisition of MS data.
Synthesis
The 2-(phenylseleno)-benzaldehyde, intermediate was synthesized
according to a known literature [40]
.
Synthesis of HemiSe. To a stirred solution of(E)-1,1,3-trimethyl-2-(2-
(phenylselanyl)styryl)-1H-benzo[e]indol-3-ium To a well-stirred solution of
aldehyde (0.090 g, 0.343 mmol) in 10 mL of dry EtOH was added 1,1,2,3-
tetramethyl-1H-benzo[e]indolium hexafluorophosphate (0.140 gm, 0.378
mmol) at room temperature. The resulting mixture was then stirred at room
temperature for 15 min. The mixture was then refluxed for 12 h to yield a
dark red mixture. The resulting residue was treated with aqueous HCl (1M,
1 mL), H2O (4 mL), and EtOAc (10 mL). The mixture was warmed to room
temperature and diluted with CH2Cl2. The mixture was washed with water,
brine and dried with drying agent (MgSO4), and the solvents volatiles were
then evaporated. The residue was purified by silica gel column
chromatography using CH2Cl2/MeOH (9:1) as an eluent to give HemiSe
(0.100 g, 63 %) as a dark orange solid. IR (CHCl3): υmax 3424 (s), 3020
(w), 2923 (m), 1698 (w), 1652 (w), 1635 (w), 1558 (m), 1540 (m), 1396
(m), 1317 (s), 1216 (w), 840 (m), 757 (s) cm-1; 1H NMRS (600 MHz,
CD2Cl2): δ 8.86 (d, JH-H = 16.3 Hz, 1H), 8.26 – 8.19 (m, 2H), 8.17 (d, JH-H
= 8.8 Hz, 1H), 8.11 (d, JH-H = 8.2 Hz, 1H), 7.85 – 7.78 (m, 2H), 7.77 (d, JH-
H = 9.0 Hz, 1H), 7.72 (t, JH-H = 7.6 Hz, 1H), 7.67 – 7.57 (m, 2H), 7.57 – 7.49
(m, 1H), 7.47 – 7.41 (m, 1H), 7.41 – 7.35 (m, 2H), 7.32 (t, JH-H = 7.6 Hz,
2H), 7.27 (d, JH-H = 7.1 Hz, 1H), 4.23 (s, 3H), 1.89 (s, 6H). 13C NMRS (150
MHz, CDCl3): 183.1, 152.7, 138.7, 137.2, 136.3, 135.0, 134.8, 134.1,
133.9, 131.8, 131.4, 131.0, 130.3, 130.0, 129.9, 129.8, 128.8, 128.7,
127.8, 127.5, 122.9, 113.1, 112.0, 54.3, 34.8, 25.9. 77Se NMRS (76.5 MHz,
CDCl3): 366.82. MS/EI m/z: Calculated for C29H26NSe is 468.1230 found
468.1286.
Keywords: superoxide radicals • fluorescence • live cell imaging
• phenylselenide • reactive oxygen species
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Acknowledgements
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