Paper
RSC Advances
st
The initial adsorption (1 cycle) for isoquinoline and quinoline
were 95% and 85%, respectively (Fig. 14). Desorption of adsor-
bed quinoline and isoquinoline from [DBN-co-STY] nanobers
was achieved by washing [DBN-co-STY] nanobers with
a mixture of excess warm water/ethanol (1 : 1).
7 N. T. McDougal, W. L. Trevellini, S. A. Rodgen, L. T. Kliman
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1
25, 12094–12095.
Conclusions
1
1 F. Toda, M. Senzaki and R. Kuroda, Chem. Commun., 2002,
0
0
1788–1789.
1
1
,1 -Binaphthyl-2,2 -diol/quinoline adduct (BINOL/QUN) and
0
0
12 S. G. Telfer and R. Kuroda, Coord. Chem. Rev., 2003, 242, 33–
6.
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,1 -binaphthyl-2,2 -diol/isoquinoline adduct (BINOL/ISOQUN)
4
are held by strong hydrogen bonds (O2–H2/O3), (O3–H3/
N1) and (O2–H2/O1), (O1–H1/N1), (O2–H2/O1) respectively.
Computationally optimized BINOL/QUN and BINOL/ISOQUN
conrmed that interaction between BINOL–quinoline and
BINOL–isoquinoline took place through electron transfer and
via hydrogen bonding. It was discovered that the HOMO posi-
tions of BINOL/QUN and BINOL/ISOQUN are localized around
BINOL, while the LUMO is positioned on quinoline and iso-
quinoline. BINOL was hosted on a polymer which was electro-
spun into nanobers. [DBN-co-STY] polymer nanobers
exhibited selectivity for quinoline and isoquinoline in a model
1
1
2
4 G. J. Kemperman, R. de Gelder, F. J. Dommerholt,
P. C. Raemakers-Franken, A. J. H. Klunder and
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1
429.
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1
1
2
2
ꢀ1
17 A. S. Ogunlaja, M. J. Coombes, N. Torto and Z. R. Tshentu,
React. Funct. Polym., 2014, 81, 61–76.
8 J. R. Katzer and R. Sivasubramanian, Catal. Rev.: Sci. Eng.,
simulated fuel with an adsorption capacity of 2.2 and 2.4 mg g
respectively. The adsorption study showed a higher selectivity
towards isoquinoline as compared to quinoline. A total of 95%
and 85% isoquinoline and quinoline was extracted in a model
simulated fuel containing a mixture of naphthalene, 1-benzo-
thiophene, dibenzothiophene, carbazole, isoquinoline and
quinoline (Fig. 16). The higher selectivity towards isoquinoline
as compared to quinoline was attributed to more favourable
electronic properties (HOMO–LUMO properties) of isoquino-
line. Computational analyses showed that carbazole–BINOL
adduct could only be formed via p–p stacking of carbazole and
1
1
2
2
2
2
2
1979, 20, 155–208.
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0, 5024–5028.
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2
2 S. Leavitt and E. Freire, Curr. Opin. Struct. Biol., 2001, 11,
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0
0
1
,1 -binaphthyl-2,2 -diol (BINOL), and this is understood to be
a weak interaction. This concept shows the ease of separating
isoquinoline and quinoline from similar compounds in fuel.
Acknowledgements
25 X. Wang, E. Matei, A. M. Gronenborn, O. Ramstrom and
M. Yan, Anal. Chem., 2012, 84, 4248–4252.
We are thankful for nancial support provided by Sasol (Pty)
Ltd. The South African National Research Foundation (NRF) is
also acknowledged for funding A. S. Ogunlaja (Green Economy
Postdoctoral Scholarship). The authors thank the Center for
High Performance Computing (CHPC), Cape Town, South
Africa for providing the platform in carrying out the molecular
modelling studies on the Gaussian09 soware.
2
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