Unexpectedly low affinity of aromatic disulfides for π-stacking interactions of the arene-polyfluoroarene type

Article abstract of DOI:10.1016/j.jfluchem.2006.02.007

1,2,3,4,5-Pentafluorodiphenyl disulfide (1) was synthesized from C₆F₅SCl and C₆H₅SSiMe₃ in quantitative yield. The homo-crystals of disulfide 1 and co-crystals of 1,1′,2,2′,3,3′,4,4′,5,5′-decafluorodiphenyl disulfide (2) with naphthalene (stoichiometry 1:2, complex 4) and diphenyl disulfide (3) with octafluoronaphthalene (stoichiometry 2:1, complex 5) were prepared followed by XRD characterization. In the crystal lattice of 1, face-to-face and face-to-edge Ph_H/Ph_F orientations of neighboring rings were observed together with face-to-edge Ph_F/Ph_F orientations. For the face-to-face Ph_H/Ph_F orientation, the large offset of Ph_H and Ph_F groups excludes their π-stacking interaction which is very non-typical of the field. The crystal lattice of 4 reveals standard π-stacking interactions of the arene-polyfluoroarene type. While in the lattice of 4 each Ph_F ring interacts alternating with naphthalenes, in 5 two disulfides 3 are bridged by one octafluoronaphthalene with only one of the Ph_H rings of each disulfide interacting with the polyfluoroarene π-system. The large offset of neighboring molecules excludes however their π-stacking interactions in complex 5. An attempt to prepare 2/3 co-crystals failed.

Full text of DOI:10.1016/j.jfluchem.2006.02.007

Journal of Fluorine Chemistry 127 (2006) 746–754
www.elsevier.com/locate/fluor
Unexpectedly low affinity of aromatic disulfides for p-stacking
interactions of the arene–polyfluoroarene type
Irina Yu. Bagryanskaya a, Yuri V. Gatilov a, Enno Lork b,
b,
Rudiger Mews , Andrey V. Zibarev
*
a,c,**
¨
a Institute of Organic Chemistry, Russian Academy of Sciences, 630090 Novosibirsk, Russia
b Institute of Inorganic and Physical Chemistry, University of Bremen, 28334 Bremen, Germany
c Department of Physics, Novosibirsk State University, 630090 Novosibirsk, Russia
Received 18 November 2005; received in revised form 9 February 2006; accepted 12 February 2006
Available online 6 March 2006
Abstract
1,2,3,4,5-Pentafluorodiphenyl disulfide (1) was synthesized from C6F5SCl and C6H5SSiMe3 in quantitative yield. The homo-crystals of
disulfide 1 and co-crystals of 1,10,2,20,3,30,4,40,5,50-decafluorodiphenyl disulfide (2) with naphthalene (stoichiometry 1:2, complex 4) and diphenyl
disulfide (3) with octafluoronaphthalene (stoichiometry 2:1, complex 5) were prepared followed by XRD characterization. In the crystal lattice of
1, face-to-face and face-to-edge PhH/PhF orientations of neighboring rings were observed together with face-to-edge PhF/PhF orientations. For the
face-to-face PhH/PhF orientation, the large offset of PhH and PhF groups excludes their p-stacking interaction which is very non-typical of the field.
The crystal lattice of 4 reveals standard p-stacking interactions of the arene–polyfluoroarene type. While in the lattice of 4 each PhF ring interacts
alternating with naphthalenes, in 5 two disulfides 3 are bridged by one octafluoronaphthalene with only one of the PhH rings of each disulfide
interacting with the polyfluoroarene p-system. The large offset of neighboring molecules excludes however their p-stacking interactions in
complex 5. An attempt to prepare 2/3 co-crystals failed.
# 2006 Elsevier B.V. All rights reserved.
Keywords: Stacking interactions; Supramolecular synthons; Self-assembled monolayers; Crystal engineering; X-ray structures
1. Introduction
and polyfluoroaromatic compounds including variously func-
tionalized derivatives ([2,4,6,7,10] and references therein). In
particular, much attention has been paid to co-crystals of
octafluoronaphthalene and C6H5–X–C6H5 compounds (X = –
[4], –CH CH– [2], –N N– [2], –CBBC– [6,7]) along with
homo-crystals of C6F5–X–C6H5 derivatives (X = – [9], –
CH CH– [8], –CH N– [3], –CBBC– [5,8]). According to our
knowledge related complexes and individual compounds with
X = –S–S– have never been investigated in this context.
Compounds of the C6F5–S–S–C6H5 type can be precursors
in the preparation of self-assembled monolayers (SAMs) of
aromatic thiolates on gold surfaces [11]. The aromatic and
aliphatic thiolate SAMs are promising components for
nanoscience and nanotechnology [11]. Although these SAMs
exhibit a high degree of structural order (i.e. true 2D
translational order), some properties are not well-controlled.
Various defects (for example, conformational arrangements)
disturb their ideally single-crystalline packing and affect their
properties [11]. In particular, aromatic thiolates with short
backbones do not form well-oriented SAMs and it is necessary
Non-bonding interactions are effective tools for controlling
molecular conformations and packing structures in a crystal
[1]. Especially, p-stacking interactions between hydrocarbon
and fluorocarbon aromatic groups are recognized to be one of
the most general supramolecular synthons (for recent
publications, see [2–10] and references therein) important
for both fundamental and applied chemistry. In particular,
these ArH/ArF interactions are successfully used in the design
and synthesis of various advanced functional materials (see
representative references given in [2,10b]).
A large variety of geometrically both matched and
mismatched molecular complexes was prepared from aromatic
* Corresponding author. Tel.: +49 421 218 3354; fax: +49 421 218 4267.
** Corresponding author. Fax: +7 383 330 9752.
E-mail addresses: mews@chemie.uni-bremen.de (R. Mews),
zibarev@nioch.nsc.ru (A.V. Zibarev).
0022-1139/$ – see front matter # 2006 Elsevier B.V. All rights reserved.
doi:10.1016/j.jfluchem.2006.02.007

I.Y. Bagryanskaya et al. / Journal of Fluorine Chemistry 127 (2006) 746–754
747
to use at least terphenyl derivatives in preparing practically
interesting thioaromatic SAMs with high degree of molecular
orientation [12].
The aim of this work is a preliminary estimation of the
prospects of p-stacking interactions of the ArH/ArF type in
controlling the structural order of aromatic disulfides since a
similar ordering might be adopted by thiolate SAMs. For this
purpose C6H5SSC6H5/C10F8 and C6F5SSC6F5/C10H8 co-crys-
tals and C6F5SSC6H5 homo-crystals were prepared followed
by XRD characterization. An attempt to prepare C6H5SSC6H5/
C6F5SSC6F5 co-crystals failed.
2. Results and discussion
Low-temperature crystallization of 1 (mp 22 8C) from
hexane gave crystals which were not suitable for XRD. High-
quality single crystals of 1 were prepared by crystallization
from its melt.
2.1. Preparations
In this work, 1,2,3,4,5-pentafluorodiphenyl disulfide (1)
[13] was synthesized from C6F5SCl and C6H5SSiMe3 in
quantitative yield, similar to the reported preparation of non-
symmetric disulfides from ArSCl and Ar0SSnBu3 [14].
Previously, 1 was obtained by heating of a 1:1 mixture of
the symmetric disulfides C6F5SSC6F5 (2) and C6H5SSC6H5 (3)
[15]:
An attempt to prepare co-crystals of disulfides 2 and 3 by
low-temperature crystallization of their 1:1 mixture from
hexane failed, only individual 2 and 3 were identified in the
solid phase. On the other hand, co-crystals of 2 with naph-
thalene (molar ratio 1:2, complex 4) and 3 with octafluor-
onaphthalene (molar ratio 2:1, complex 5) were obtained by
Table 1
Crystal data and structure refinement for 1, 4 and 5
Compound
1
4
5
Empirical formula
Formula weight
Temperature (K)
Wavelength (pm)
Crystal system
Space group
C12H5F5S2
308.28
C32H16F10S2
654.57
C34H20F8S4
708.74
173 (2)
243 (2)
173 (2)
71.073
71.073
71.073
Orthorhombic
Pna21
Monoclinic
P21/c
Monoclinic
P21/c
Unit cell dimensions
a (pm)
1097.0 (2)
724.00 (7)
1669.7 (5)
b (pm)
1278.20 (10)
2997.8 (3)
587.20 (10)
c (pm)
860.80 (10)
1328.95 (12)
104.164 (7)
1568.2 (3)
b (8)
90
95.93 (2)
Volume (nm3)
1.2070 (3)
2.7967 (4)
1.5293 (6)
Z
4
4
2
Density (calculated) (Mg mꢀ3
)
1.696
1.555
1.539
Absorption coefficient (mmꢀ1
)
0.485
0.280
0.385
F(0 0 0)
616
1320
720
Crystal size (mm3)
u range for data collection (8)
Index range
0.8 ꢁ 0.4 ꢁ 0.4
2.85–27.50
1.0 ꢁ 0.3 ꢁ 0.2
2.08–25.00
0.80 ꢁ 0.60 ꢁ 0.30
2.61–27.50
ꢀ14 ꢂ h ꢂ 14, ꢀ16 ꢂ k ꢂ
16, ꢀ11 ꢂ l ꢂ 1
6368
ꢀ8 ꢂ h ꢂ 8, ꢀ35 ꢂ k ꢂ 0,
ꢀ15 ꢂ l ꢂ 15
6826
ꢀ21 ꢂ h ꢂ 21, ꢀ7 ꢂ k ꢂ 1,
ꢀ20 ꢂ l ꢂ 1
Reflections collected
Independent reflections
Completeness to u8 (%)
Absorption correction
Refinement method
4706
1709 [R(int) = 0.0400]
99.8
4897 [R(int) = 0.0466]
99.4
3518 [R(int) = 0.0428]
99.8
None
Full-matrix least-squares on F2
Integration
Full-matrix least-squares on F2
None
Full-matrix least-squares on F2
Data/restraints/parameters
Goodness-of-fit on F2
Final R indices [I > 2s(I)]
R indices (all data)
1709/1/174
4897/0/397
3518/0/247
1.066
1.046
1.032
R1 = 0.0248, wR2 = 0.0673
R1 = 0.0266, wR2 = 0.0687
0.0071 (19)
R1 = 0.0563, wR2 = 0.1520
R1 = 0.0866, wR2 = 0.1747
0.0000
R1 = 0.0483, wR2 = 0.1243
R1 = 0.0574, wR2 = 0.1327
0.0153 (19)
Extinction coefficient
3
Largest diff. peak and hole (e A )
˚
0.209 and ꢀ0.244
0.360 and ꢀ0.310
0.614 and ꢀ0.589

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Table 2
Selected bond lengths (pm), bond and torsion angles (8) for disulfides 1–3 and for the disulfides 2 and 3 in the complexes 4 and 5 (for atom numbering, see Figs. 1, 3, 4)
S1S2
S1C1
S2C7
S1S2C7
S2S1C1
C1S1S2C7
S1S2C7C8
S2S1C1C6
1
2
204.4 (1)
205.9 (4)
206.6 (1)
176.7 (2)
177.0 (7)
176.4 (3)
177.5 (4)
–
178.9 (2)
–
106.20 (9)
–
102.32 (8)
101.3 (3)
81.45 (1)
73.62 (1)
27.2 (2)
72.8 (2)
73.21 (2)
76.37 (2)
2 in 4
–
103.9 (1)
104.95 (5)
104.76 (7)
104.7 (1)
106.19 (4)
105.22 (7)
ꢀ107.15 (17)
84.18 (5)
ꢀ100.1 (3)
163.12 (8)
ꢀ174.4 (2)
ꢀ91.3 (3)
179.4 (8)
3
203.0 (5)
203.4 (1)
180.0 (11)
178.1 (2)
3 in 5
–
ꢀ85.38 (9)
ꢀ170.7 (1)
this technique. The stoichiometry of complex 5 is rather
remarkable since the molar ratio of the starting materials used
in the preparation was 2:1 in favor of C10F8.
stacking interactions. 1 crystallizes in the polar space group
Pna21 with one molecule in the asymmetric unit. In the homo-
crystals of 1 (Fig. 2) face-to-face and face-to-edge PhH/PhF
orientations were observed together with face-to-edge PhF/PhF
orientations. For the face-to-face PhH/PhF orientation, the
interplanar separation (C5ꢃ ꢃ ꢃC10 contact, Fig. 2) is only
339.8 pm. However the large offset of PhH and PhF groups
excludes their p-stacking interactions. This is very non-typical
of the field since, based on many examples, it is accepted that
arene and polyfluoroarene moieties are always involved in p-
stacking interactions when present in the same crystal lattice
([2–10] and references therein). Several factors might
contribute to this unusual packing. The intermolecular Fꢃ ꢃ ꢃF
contact of 279.5 pm, which is in the range of the sum of the van
der Waals radii, might prevent the p-stacking in 1, the observed
edge-to-face contact F5ꢃ ꢃ ꢃC2 (300.2 pm), and the weak Hꢃ ꢃ ꢃF
contacts in the range 260–300 pm (indicated in Fig. 2) might
stabilize the packing of 1.
In contrast to 2 and 3, the corresponding diselenides do not
produce complexes with C10H8 and C10F8, respectively, under
conditions of crystallization from hexane. It should also be
noted that 3 and C6H5SeSeC6H5 do not produce complexes
with C6F6 under conditions of crystallization from the latter.
2.2. Structural investigations
In Table 1 details of the crystal structure determinations and
structure refinements of compound 1 and the complexes 4 and 5
are given. Table 2 shows selected bond lengths, bond and
torsion angles for 1 (for atom numbering, see Fig. 1), for the
disulfides 2 and 3 in complexes 4 and 5 together with the
relevant data for individual 2 and 3.
2.2.1. Solid state interactions
4 crystallizes in the space group P21/c with one molecule of
2 and two molecules of C10H8 in the asymmetric unit. These
molecules are combined to p-stacks along the a axis and each
PhF ring interacts alternating with two naphthalene molecules
The main purpose of the present paper is the investigation of
non-bonding interactions between arene and perfluoroarene
groups in the solid state, with special emphasis on the p-
Fig. 1. The molecular structure of disulfide 1. For selected bond lengths, bond and torsion angles of 1, see Table 2.

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749
Fig. 2. Orientations of neighboring molecules (above), and Hꢃ ꢃ ꢃF and Fꢃ ꢃ ꢃF interactions (below) in disulfide 1.

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Fig. 3. The structure of complex 4. For selected bond lengths, bond and torsion angles of the disulfide 2, see Table 2.
Fig. 4. ArFꢃ ꢃ ꢃAr overlap (above) and Hꢃ ꢃ ꢃF and Fꢃ ꢃ ꢃF contacts (below) in complex 4.

I.Y. Bagryanskaya et al. / Journal of Fluorine Chemistry 127 (2006) 746–754
751
Fig. 5. The structure of (above), and C–Hꢃ ꢃ ꢃp, Cꢃ ꢃ ꢃF, and Sꢃ ꢃ ꢃF interactions in (below), complex 5. For selected bond lengths, bond and torsion angles of the disulfide
3, see Table 2.

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I.Y. Bagryanskaya et al. / Journal of Fluorine Chemistry 127 (2006) 746–754
Fig. 6. View of the crystal packing of complex 5.
(Fig. 3). The interplanar separation of 341–349 pm within the
stacks is typical for arene–polyfluoroarene p-stacking inter-
actions ([2–10] and references therein). The corresponding
distances between the centers of the rings lie in the range of
362–393 pm revealing some offset of the interacting rings
(Fig. 4), which is normal. Hꢃ ꢃ ꢃF contacts between C10H8
and 2 within a 4 unit, which would be expected from Fig. 4,
are much weaker (360 pm) than the interactions between
different units. The Hꢃ ꢃ ꢃF distances indicated in Fig. 4 are in
the range of 260–300 pm.
pm), S1ꢃ ꢃ ꢃF3 (338 pm) and C–Hꢃ ꢃ ꢃp (ArF) interactions. The
shortest Fꢃ ꢃ ꢃF contacts between fluorines of C10F8 range from
287 to 296 pm. Many factors contribute to the reasons for
complex 5 being another unexpected example of negligible p-
stacking interactions between ArH and ArF groups.
2.2.2. Structural changes in aromatic disulfides on
fluorination and complexation
The data in Table 2 for the mixed disulfide 1, the
fluorocarbon disulfide 2 [16] and the hydrocarbon disulfide 3
[17] in their homo-crystals show that 1 is combined from
fragments of 2 and 3. The SS distance in 1 (204.4 (1) pm) is
intermediate between that of 2 (205.9 (4) pm) and 3 (203.0
(5) pm). The CS bonds in 2 are shorter than in 3, a similar
difference is found in 1 for S1C1 and S2C7. The angles at the
sulfur centers in 2 (101.38) are smaller than in 3 (106.28),
similar differences are found for the corresponding fragments
in 1 (102.38 and 106.28, respectively). The torsion angle C–S–
S–C in 3 is equal to 84.28, in 2 equal to 73.68, in the mixed
5 crystallizes in the space group P21/c with one molecule of
3 and 0.5 molecules of C10F8 in the asymmetric unit. In contrast
to 4, in complex 5 two disulfides 3 are linked by only one
octafluoronaphthalene, and only one PhH group of 3 is involved
in non-bonding interactions with C10F8, the second (not
interacting) PhH group is disordered (Figs. 5 and 6). Fig. 5
shows the large offset between the planes of the interacting PhH
groups of 3 and the C10F8 plane. Responsible for this offset
might be weak H1ꢃ ꢃ ꢃF5 (248.5 pm), F(ArF)ꢃ ꢃ ꢃC(Ar) (350–365

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753
species 1 81.458 is determined. According to a simple bonding
model this torsion angle is a result of the interaction of the 3p
lone pairs at the two sulfur centers which try to become
orthogonal. For the H–S–S–H molecule an angle of 90.58 was
calculated in this work at the MP2/6-31G* level of theory.
The most remarkable difference between the non-fluorinated
and the fluorinated species is observed for the torsion angles C–
C–S–S. They enlarge from 10.58 (average) in 3 to 74.88 in 2,
with the aryl groups almost parallel to the SS bond to almost
perpendicular. Compared to 3, in 1 the PhH group deviates more
from the SS plane (27.28) whilst the angle to the PhF group
slightly decreases in comparison with 2.
In complex 5 the interaction of 3 with C10F8 has almost no
influence on bond distances and bond and torsion angles.
In complex 4 the C–C–S–S torsion angles increase to almost
perpendicular (88.48), and for the C–S–S–C torsion angle a
dramatic increase from 73.68 to 107.158 4 is determined in
going from homo-crystals 2 to co-crystals 4, seemingly due to
p-stacking interactions between 2 and C10H8.
temperature the solvent was removed with syringe and the
residual solid was dried under vacuum, first at ꢀ50 8C, then at
ambient temperature. Compound 1 was obtained as white
crystals, 1.17 g (95%), mp 21–22 8C (22 8C [15]). MS, m/z:
307.9755 (M+, calculated for C12H5F5S2 307.9753). NMR, d:
1H: 7.53–7.29 (5H); 19F: 31.0 (2F), 11.8 (1F), 1.7 (2F).
According to the GC–MS analysis, the purity of 1 was 96.6%.
Crystals of 1 obtained as described above were too small to
be measured by XRD. The single crystals suitable to XRD were
prepared as follows: a drop of liquid 1 was placed into Krytox
oil (Du Pont), and the system was cooled by stream of the cold
nitrogen. Under these conditions, 1 solidified into well-shaped
big transparent crystals.
4.1.2. Complex of 1,10,2,20,3,30,4,40,5,50-decafluorodiphenyl
disulfide with naphthalene (4) and complex of diphenyl
disulfide with octafluoronaphthalene (5)
A mixture of 0.40 g (0.001 mol) of C6F5SSC6F5 and 0.26 g
(0.002 mol) of C10H8, or 0.22 g (0.001 mol) of C6H5SSC6H5
and 0.54 g (0.002 mol) of C10F8, was dissolved in 2 mL of
boiling hexane and solution was gradually cooled to 20 8C.
Complexes 4 and 5 were obtained as transparent colorless
needles: 4, 0.38 g (58%), mp 58–59 8C; 5, 0.26 g (68%), mp
55–56 8C.
3. Conclusions
Unexpectedly, aromatic disulfides revealed rather low
affinity for p-stacking interactions of the arene–polyfluoroar-
ene type. However, it follows from this work that the disulfides
can be involved in these interactions under certain circum-
stances. As a result, ArH/ArF p-stacking interactions might
have some prospects in improving structural order of thiolate
SAMs. The design and synthesis of (fluoro) aromatic disulfides
with enlarged propensity to the discussed interactions, in
particular based on the approach used in this work for preparing
1, might be a direction for further research.
The composition and stoichiometry of the complexes were
confirmed by GC–MS data.
4.2. Crystallographic analysis
The single crystal X-ray determinations (Table 1) were
carried out on a Siemens P4 diffractometer using Mo Ka
(71.073 pm) radiation. The crystals were mounted using KEL-F
oil on a thin glass fiber. The structures were solved by direct
methods and refined by full-matrix least-squares against F2 of
all data using SHELX-97 software [22]. The structures obtained
were analyzed for shortened contacts between non-bonded
atoms with the PLATON program [23].
4. Experimental
The 1H and 19F NMR spectra were measured with a Bruker
AV-300 spectrometer at frequencies of 300.13 and
282.37 MHz, respectively, for solutions in CDCl3, with TMS
and C6F6 as standards. The high-resolution mass-spectra were
recorded with a Finnigan MAT MS-8200 instrument. GC–MS
Crystallographic data (excluding structure factors) for the
structures have been deposited with the Cambridge Crystal-
lographic Data Centre as supplementary publications no.
CCDC 290029 (1), CCDC 290030 (4) and CCDC 290028 (5).
Copies of data can be obtained, free of charge, on application to
CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44
1223 336 033 or E-mail: deposit@ccdc.cam.ac.uk).
measurements were performed with a Hewlett-Packard
G1800A GCD device for solutions in CH2Cl2.
4.1. Compounds
Compounds C6F5SSC6F5 (2) [18], C6F5SCl [19],
C6H5SSi(CH3)3 [20], and C6F5SeSeC6F5 [21] were prepared
as described before. Compounds C10F8, C10H8, C6H5SSC6H5
and C6H5SeSeC6H5 were commercially available (Aldrich).
Acknowledgements
The authors are grateful to Mr. Peter Brackmann for his
assistance in the XRD experiments, and to the Deutsche
Forschungsgemeinschaft, Germany, for financial support of this
work (project 436 RUS 113/486/0-3 R).
4.1.1. 1,2,3,4,5-Pentafluorodiphenyl disulfide (1)
At 20 8C and under argon, a solution of 0.94 g (0.004 mol) of
C6F5SCl in 5 mL of Et2O was added dropwise to a stirred
solution of 0.73 g (0.004 mol) of C6H5SSi(CH3)3 in 5 mL of the
same solvent. After 1 h, the solvent was distilled off under
reduced pressure, the residue was dissolved in 2 mL of hexane
and solution was placed into cryostat at ꢀ50 8C. At the same
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