Semithiobambus[6]uril is a Transmembrane Anion Transporter
Chao Lang,
a
Amar Mohite,
b
Xiaoli Deng,
a
Feihu Yang,
a
Zeyuan Dong,
a
Jiayun Xu
a
, Junqiu Liu*
,a
Ehud Keinan*
,c
and Ofer Reany*
, b
Table of Contents
Content Page
General information S1
Materials S1
Instruments S2
Procedure for anion transport experiments S2
Carboxyfluorescein (CF) assay S5
Fluorescence titration experiments S6
Determination of ion selectivity S6
Cation selectivity assay S7
Electrophysiology measurement S8
References S8
1. General information
Materials
All bambusurils 2-5 used in this work were synthesized and fully characterized
according to previously reported procedures.
[1-3]
Bumbus[6]uril, 2:
[1]
With TBACl:
1
H NMR (400 MHz, CDCl
3
): = 5.41 (12 H), 5.18 (12 H), 3.15 (36 H).
Semithio-bambus[6]uril, 3:
[2]
M.p > 395 ˚C (dec.).
1
H NMR (400 MHz, [D
6
]DMSO): = 5.13 (bs, 12 H, CH), 4.87
(bs, 12 H, CH
2
), 2.84 (bs, 36 H, CH
3
); HRMS (TOF/ESI+), m/z calcd for
C
42
H
60
N
24
O
6
S
6
: 1188.3452; found: 1188.3470.
Semiaza-bambus[6]uril, 4:
[3]
In the form of a polyiminium n(triflate)/bromide salt:
1
H NMR (400 MHz,
[D
6
]DMSO): = 8.22 (s, 6 H, NH), 5.73 (s, 12 H), 5.06 (s, 12 H), 3.30 (s, 36 H), 3.04
ppm (s, 18 H);
13
C NMR (100 MHz, [D
6
]DMSO) = 159.6, 158.1, 73.3, 47.7, 34.3,
30.9 ppm;
19
F NMR (376 MHz, [D
6
]DMSO): = 77.9 ppm.
Then, to afford the free base semiaza-bambus[6]uril derivatives we performed
neutralization reaction using the polyiminium triflate salt of semiaza-bambus[6]uril
(50 mg) and Amberlyst A26 (OH
-
form, 50 mg) suspended in methanol (20 mL), and
the mixture was stirred at room temperature for 15 min. After filtration the clear
S1
Electronic Supplementary Material (ESI) for ChemComm.
This journal is © The Royal Society of Chemistry 2017