A Supramolecular Off-On Fluorescent Switch and
IMPLICATION Logic Gate for Detection of Cationic
Surfactant
Junhong Qian 1,2 Yufang Xu 1 Shitong Zhang 1 Xuhong Qian* 1
1 State Key Laboratory of Bioreactor Engineering and Shanghai Key Laboratory of Chemical Biology, School of
Pharmacy, East China University of Science and Technology, Shanghai 200237, China;
2
School of Chemistry and
Molecular Engineering, East China University of Science and Technology, Shanghai 200237, China xhqian@ecust.edu.cn
(Xuhong Qian)
Supporting Information
Contents
Synthesis---------------------------------------------------------------------------------------------------------P2
SDS effect on the spectral properties of P1 ------------------------------------------------------------------P3
CTAB effect on the UV-vis spectrum of P1 -SDS aqueous solution---------------------------------------P4
CTAB effect on the UV-vis spectrum and 
F
of P1 ---------------------------------------------------------P5
UV-vis spectra of P1 under the different conditions---------------------------------------------------------P6
The maxima of absorbance and 
F
of P1 -SDS under different conditions--------------------------------P7
1

Synthesis
N-(aminoethyl)-4-bromonaphthalene-1,8-dicarboximide (1) : Ethylenediamine (2.0 g, 33.3 mmol) was added to a suspension of 4-bromonaphthalene-1,8-dicarboximide (5.54 g, 20 mmol) in ethanol (50 mL). The mixture was then refluxed for 4 hrs, after which the solvent was evaporated under vacuum.
The product crystallized from ethanol. Yield 85%. M.p. 154.8-155.2

C; MS: m/z (%) 318 (1%); 1H
NMR (500 MHz, CDCl
3
):

8.65 (dd, 1H, 7-ArH), 8.56 (dd, 1H, 2-ArH), 8.41 (d, J = 7.9 Hz, 1H, 5-
ArH), 8.02 (d, J = 7.8 Hz, 1H, 5-ArH), 7.82 (dd, 2H, 3,6-ArH), 4.27 (t, J = 6.6 Hz, 2H, -NCH
2
CH
2
NH
2
),
3.07 (t, J = 6.6 Hz, 2H, -NCH
2
CH
2
NH
2
).
P1 : To a solution of 5 mL of ethylene glycol monomethyl ether added 0.2 g (6.3 mmol) of 1 and excess n-dodecyl amine (0.3 g). The mixture was refluxed for 5 hrs under N
2
atmosphere and then the solvent was evaporated under vacuum. The product was purified by chromatography using methanol/ dichloromethane (1: 100, v/v) as eluant to give 105 mg (45%) of P1 as orange red solid: 1H-NMR
(CDCl
3
-MD
3
OD) 8.34 (d, J = 7.2 Hz, 2H), 8.18 (d, J = 8.4 Hz, 1H), 7.54 (t, J = 8.0 Hz, 1H), 6.67 (d, J =
8.8 Hz, 1H), 4.11 (s, 4H), 3.36 (m, 2H), 1.76 (m, 2H) , 1.47 (m, 2H), 1.34 (m, 16H), 0.86 (t, J = 6.5 Hz,
3H), 13C-NMR (100 MHz) δ161.6, 156.1, 150.2, 131.0, 130.7, 129.3, 127.6, 124.3, 123.1, 121.1, 104.3,
104.2, 50.9, 43.6, 43.5, 31.8, 29.5, 29.4, 29.3, 29.2, 28.4, 27.1, 22.5, 13.6 ppm. HR-MS (ES+) Calcd for
([M+H]) + , 406.2858; Found, 406.2841.
2

0.08
0.06
0.04
0.02
SDS

M 0
7.2
a
0.00
250 300 350 400 450 500 550 600

(nm)
1.5
1.2
[SDS]

M
0 b
0.9
0.6
7.2
0.3
0.0
450 500 550 600

(nm)
650 700
Figure S1 SDS effect on the UV- vis (a) and emission (b) spectra of P1 ([ P1 ] = 6.0  M,  ex
= 445 nm).
3

0.20
0.16
0.12
0.08
0.04
0.00
a
CTAB 150 mM
0
360 390 420 450 480

/ nm
510 540 570 600
0.18
0.15
0.12
0.09
0.06
b
0.03
0 30 60 90
[CTAB] /

M
120 150
Figure S2 CTAB effect on the UV-vis spectrum of P1 -SDS aqueous solution (a) and CTAB titration curve (b) ([SDS] / [ P1 ] =10:1, [ P1 ] = 6  M,  ex
= 445 nm).
4

0.20
0.16
0.12
0.08
0.04
0.00
[CTAB] mM
0.48
0 a
280 350 420

(nm)
490 560
0.19
0.18
0.17
0.16
0.15
0.14
b
0.13
0.12
0.0
0.1
0.2
0.3
0.4
0.5
0.6
[CTAB] 10
-3
mol/L
0.7
0.8
0.9
Figure S3 CTAB effect on the UV-vis spectrum (a) and 
F
(b) of P1 .
5

0.20
0.16
0.12
0.08
0.04
0.00
1
0
inputs outputs
SDS CTAB T A470 
F
0 0 0 0.149 (1) 310 (1)
0 0 1 0.151 (1) 318 (1)
0 1 0 0.152 (1) 371 (1)
0 1 1 0.176 (1) 444 (1)
1 0 0 0.048 (0) 4.5 (0)
1 0 1 0.122 (1) 249 (1)
1 1 0 0.175 (1) 351 (1)
1 1 1 0.168 (1) 329 (1)
-0.04
350 400 450

/ nm
500 550 600
Figure S4 UV-vis spectra of P1 in water under the eight experimental conditions required to demonstrate three-input IMPLICATION logic ([SDS] is 0 (low, 0) or 10  M (high, 1), [CTAB] is 0
(low, 0) or 20  M (high, 1) and the temperature is 25  C (low, 0) or 75  C (high, 1); [ P1 ] = 6  M).
6

Table 1 the maxima of absorbance A and fluorescence quantum yield 
F
of SDS/ P1 system in the presence of enough CTAB or at higher temperature (90  C) ([ P1 ] = 6  M,  ex
= 445 nm) external stimulate
CTAB temperature
A max

F
A max

F
6 initial [SDS] /  M
0.188
0.172
0.125
60
0.172
0.156
0.108
180
0.166
0.121
0.093
0.112 0.103 0.089
Acknowledgement : This work was financially supported by the Science and Technology Foundation of
Shanghai.
7