Induction of chirality in 4,4′-azopyridine by halogen-bonding interaction with optically active ditopic donors

Article abstract of DOI:10.1039/c8nj05750h

Optically active ditopic halogen bond donors bearing two 4-iodotetrafluorophenyl groups were obtained by reaction of chiral diols with iodopentafluorobenzene. Co-crystallization of these donors with anti-4,4′-azopyridine afforded binary complexes containing infinite chains of the alternating component molecules connected by halogen bonds. The solid state CD measurements confirmed that complexation induces optical activity of the azo chromophore due to the twisting of the aryl-N═N system or external chiral perturbation exerted by host molecules.

Full text of DOI:10.1039/c8nj05750h

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PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
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Induction of chirality in 4,4’-azopyridine by halogen-bonding
interaction with optically active ditopic donors
Jan Alfuth,a Jarosław Chojnacki,b Tadeusz Połońskia and Teresa Olszewska*a
Received 00th January 20xx,
Accepted 00th January 20xx
Optically active ditopic halogen bond donors bearing two 4-iodotetrafluorophenyl groups were obtained by reaction of chiral
diols with iodopentafluorobenzene. Co-crystallization of these donors with anti-4,4’-azopyridine afforded binary complexes
containing infinite chains of the alternating component molecules connected by halogen bonds. The solid state CD
measurements confirmed that complexation induces optical activity of the azo chromophore due to the twisting of the
aryl–N=N system or external chiral perturbation exerted by host molecules.
DOI: 10.1039/x0xx00000x
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due to a dissymmetry created by a chiral environment or upon
assuming a chiral conformation. An asymmetric perturbation of
the chromophore leads to induced circular dichroism (ICD),
whose magnitude depends on the mutual arrangement of the
host and guest molecules.13
In this account, we wish to report a new possibility of
inducing optical activity in the azo chromophore by using
halogen bonded assemblies of anti-4,4’-azopyridine (apy) with
chiral ditopic halogen bond donors 1–3 (Scheme 1). The induced
optical activity of the azo chromophore was detected by solid
state CD measurements.
Azo-dyes, particularly those related to azobenzene, undergo
photoinduced syn–anti isomerization that is responsible for
their potential application in optical switches and sensors,
reversible data storage,14 photoresponsible supramolecular
systems,15 or liquid crystalline polymers.16 Photochromic
Introduction
The controlled arrangement of molecules in a predictable
fashion to generate supramolecular assemblies that can exhibit
properties not presented by isolated components long has been
an area of interest in material chemistry.1 Many multi-
component supramolecular structures have been designed and
obtained using non-covalent interactions such as hydrogen and
halogen bonds or π-π interactions.2-4 Particularly, halogen
bonding has attracted intense interest in recent years as an
useful tool in the field of crystal engineering.4 It has been
presented as an attractive interaction between an electrophilic
region of halogen atom (σ-hole) and nucleophilic region of
another molecule.5 Due to the strength and directionality of
halogen bonding interactions they could be used as an
alternative to hydrogen bonding.4 Thus many new examples of
halogen bond donors have been developed as substrates in
preparation of ordered solids with designed architecture.
Among variety of structures chiral components able to engage
in halogen bonds are extremely rare.6 Crystalline materials with
chiral framework are of interest because of their potential
application in the field of optical resolution,7 asymmetric
syntheses,8 photochirogenesis,9 nonlinear optics10 or chiral
molecular conductors.11 Furthermore, chiral solid phases
exhibit intriguing spectroscopic properties. A phenomenon of
induced optical activity arises when an achiral guest molecule is
complexed by a chiral host. Optical activity can be induced upon
dissolution of an achiral solute in a chiral solvent, by inclusion
complexation of achiral guest in the cavity of a chiral host or by
chirality transfer between chiral and achiral components in
supramolecular polymers.12 The guest becomes optically active
a.Department of Organic Chemistry, Gdańsk University of Technology, 80-233
Gdańsk, Poland. E-mail: teresa.olszewska@pg.edu.pl
b.Department of Inorganic Chemistry, Gdańsk University of Technology, 80-233
Gdańsk, Poland. E-mail: jaroslaw.chojnacki@pg.edu.pl
Scheme 1. The structures of ditopic halogen bond donors
azopyridine (apy).
1–3 and anti-4,4’-
† Electronic Supplementary Information (ESI) available: NMR spectra (1H, 13C, 19F)
and HRMS for all final products, experimental details, geometry of halogen bonds
and crystal structures of all complexes. See DOI: 10.1039/x0xx00000x
This journal is © The Royal Society of Chemistry 20xx
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properties of crystalline azobenzenes are inspiring for interest
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Triclinic crystals of apy·(S,S)-1b, space group P1, contain
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in structural investigations of azobenzene solids. In that infinite almost linear chains of the alDteOrI:n1a0t.i1n0g39/cCo8mNJp0o5n75e0nHt
context, we have recently demonstrated induced optical molecules connected by halogen bonds (Fig. 1) and spreading in
activity of the azobenzene chromophore by inclusion [–3 1 1] direction. Asymmetric unit contains two independent
complexation by chiral hosts as well as by hydrogen-bonded apy and two (S,S)-1b molecules. Substantial differences
assembly with optically active dicarboxylic acids.17
between symmetry independent (S,S)-1b molecules can be
found in conformation of 5-membered C3O2 rings: one is close
to envelope on C8 (see Figure S13 , ESI) while the second is
rather twisted on C40-O9 (found by Platon19 program). The
halogen bonds connecting apy with (S,S)-1b are nearly linear
(see Table 1) and quite strong as evidenced by the I···N distances
of ca 2.8 Å (80% of the sum of the van der Waals radii of I and
N).20 The molecule of (S,S)-1b adopts a partially folded
conformation where one of the iodotetrafluorophenyl rings is
located over the central cyclohexane ring and the second one
pointing outside. The azopyridine apy molecule is slightly
deviated from planarity caused by twisting of one the pyridine
rings from the plane of the azo group (the corresponding C=C–
N=N torsional angles are below 9° for both entities, see Table
2). The parallel orientation of the halogen bonded chains of
apy·(S,S)-1b enable face-to-face π-π stacking interactions
between the fluoroaryl rings of (S,S)-1b between two neighbour
molecules (the distance between the centroids of the
neighbouring rings is of ca 3.7 Å, see Fig. 4a) that results in an
additional stabilization of the structure.
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Results and discussion
Ditopic halogen bond donors 1–3 were obtained by reaction
of chiral diols with iodopentafluorobenzene in DMF solution
using NaH or Cs2CO3 as a base following literature proce-
dures.6a-b Optically active diols (S,S)-4 and (S,S)-5 were prepared
by LiAlH4 reduction of corresponding dicarboxylic esters
(Scheme 2 and Scheme 3). 4,4’-Azopyridine (apy) was obtained
by oxidative coupling of 4-aminopyridine with sodium
hypochlorite solution.18
Single crystals of the molecular complexes were grown by a
slow evaporation of an equimolar amounts of the components
from a CH2Cl2–heptane solution. Diffraction quality crystals
were obtained for the complexes apy·(S,S)-1b, apy·(S,S)-2 and
apy·(R)-3 and their crystal structures were determined by
single-crystal X-ray diffraction. Unfortunately the complex
apy·(S,S)-1a did not afford any good quality crystals, however,
it does not pose any difficulty in the solid state CD
measurements.
The complex apy·(S,S)-2 crystallizes in the orthorhombic
system, space group P212121, and is composed of infinite zig-zag
chains of halogen bonded alternating component molecules
(the I∙∙∙N distances of ca 2.8 Å and the C–I···N angles of ca 173°).
The cyclohexane ring of (S,S)-2 adopts a chair conformation
with equatorially oriented aryloxymethyl groups (Fig. 2).
Fig. 1. Molecular structure of apy·(S,S)-1b. Hydrogen atoms omitted, atom
labelling scheme given for selected atoms in the asymmetric unit. Four symmetry
equivalent atoms (N4, N8, I2 and I4) added to show chains of halogen bonding,
pointed by dotted lines. Symmcodes for N4 and N8: (3+x, –1+y, –1+z), for I2 and
I4: (–3+x, 1+y, 1+z).
Scheme 2. The synthesis of ditopic halogen bond donors (S,S)-1a–b: (a) 2,2-
dimethoxypropane (for (S,S)-1a) or cyclohexanone (for (S,S)-1b), pTSA; (b) LiAlH4,
THF, then H2O; (c) Cs2CO3, CF5I; (d) NaH, CF5I.
Table 1. Halogen bonding parameters: contact lengths I···N [Å] (upper value) and angles
C–I···N [°] (lower value), found in the investigated structures. Symmetry equivalent
atoms were used for N4 and N8.
apy·(S,S)-1b
apy·(S,S)-2
apy·(R)-3
Independent entities Z’
2
1
1
2.826 (7)
175.2 (2)
2.814 (5)
172.7 (2)
2.800 (7)
171.2 (3)
C–I1···N3
2.844 (8)
170.1 (3)
2.815 (5)
173.2 (3)
2.813 (7)
173.1 (3)
C–I2···N4
C–I3···N7
C–I4···N8
2.850 (7)
172.4 (3)
-
-
-
-
Scheme 3. The synthesis of ditopic halogen bond donor (S,S)-2: (a) MeOH, H2SO4;
(b) LiAlH4, THF, then H2O; (c) NaH, CF5I.
2.777(7)
179.0 (3)
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Journal Name
The apy molecule adopts almost exactly the Ci (
with the pyridine rings twisted from the azo group plane by as stacking of parallel zig-zag chains and apy·(R)-3 as stacking of
alternating angles ca 13° and very small dihedral angle between layers with parallel chains, but with alternating direction of
the aromatic rings (see Table 2). The 1D chains of apy·(S,S)-2 are chains every second layer (see Fig. 4). Zig-zag chains of
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̅
1
) symmetry parallel straight chains within the entire structure, apy·(S,S)-2
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DOI: 10.1039/C8NJ05750H
further organized into dense packed 2D corrugated layers by apy·(S,S)-2 spread along screw axis, so they obey
face-to-face π-π stacking interactions between the fluoroaryl symmetry.23a Table 3 lists the relevant crystallographic data for
퓅21 rod group
units of (S,S)-2 and pyridine rings of apy (the distance between the complexes apy·(S,S)-1b
the centroids of the rings is of ca 4.25 Å, see Fig. 4b) occurring
between the neighbouring chains. The pyridyl–perfluoroaryl a)
stacking interactions are important stabilizing forces for various
supramolecular structures which are capable in cooperation
with halogen bonding to direct the crystal packing of binary
molecular complexes.21,22
The crystal structure of the complex apy·(R)-3 (space group
P212121) revealed infinite chains of halogen bonded component
molecules (the I···N distances are of ca 2.8 Å and the C–I···N
angle is above 170°) (Fig. 3). The molecules of (R)-3 adopt
strongly folded conformation resulting from a pair of face-to-
face π-π stacking interactions between the fluoroaryl and
naphthalene rings (the distance between the centroids of the
neighbouring 6-membered fused rings is of ca 3.5 Å, see Table
, apy·(S,S)-2 and apy·(R)-3.
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1 in ESI) which is very similar to that reported for the isolated
(R)-3 molecule.6a
b)
The guest apy molecule assumes a twisted conformation of
almost C2 symmetry (the corresponding C=C–N=N torsional
angles are of 13.09 and 14.00°, see Table 2). The crystal packing
reveals face-to-face π-π stacking interactions between the
fluoroaryl units and pyridine rings and also between the
naphthalene and pyridine rings of the host and guest molecules
(Table 1, ESI).
Due to different conformational geometry of the ditopic
donors, packing of chains of the compounds is different in each
case. Crystal packing in apy·(S,S)-1b, can be described as
stacking of
c)
Fig. 2. Atom labeling scheme for selected atoms in asymmetric unit of apy·(S,S)-2
.
Two symmetry equivalent N4 (½ – x, –y , ½ + z) and I2 (½ – x, –y , –½ +z) atoms
added to show the directions of halogen bonding.
Fig. 4. Crystal packing of apy complexes: a) apy·(S,S)-1b, view perpendicular to the
chains (green and red apy, blue and yellow (S,S)-1b symmetry independent
̅ ̅
molecules), all the chains are parallel to [3 1 1] in the entire structure, b) apy·(S,S)-
2, viewed along [100] direction, parallel zig-zag chains clearly dominate the
packing with translation period along [001] c) apy·(R)-3, viewed along [001], two
̅
linear chains spread in parallel layers in directions [2 1 0] and [2
1
0].
Fig. 3. Asymmetric unit of apy·(R)-3, with selected atom labels. Hydrogen atoms
are omitted for the clarity. Halogen bonding pointed by dotted lines and
completed with symmetry equivalent atoms I2 (–2+x, 1+y, z) and N4 (2+x, –1+y,
z).
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DOI: 10.1039/C8NJ05750H
Table 2. Geometrical parameters indicating conformational changes of apy molecules in crystalline state. (Crystals with only apy molecules26 contain inversion centre between N
atoms in the azo group, exactly Ci symmetry, causing alternation the torsions and setting the dihedral angle between aromatic rings to zero).
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Structure
apy·(S,S)-1b
apy·(S,S)-2
apy·(R)-3
apy (190K)26
apy (298K)26
Smallest torsions
C=C–N=N [°]
–5.6(12) and –2.6(11)*
0.5(12) and 8.9(12)†
13.1(10) and –13.5(10)
14.0(10) and 13.1(10)
+14.74 and –14.74
+17.77 and –17.77
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Dihedral angle between
the aromatic rings [°]
8.3(4)*
8.6(5)†
0.84
29.33
0
0
*for N1-N2; †for N5-N6
The CD spectra of crystalline supramolecular complexes in
combination with X-ray studies have recently emerged as an
useful technique for elucidation of the mechanisms of induction
of optical activity.24,25 Thus we measured the solid state CD
spectra of the complexes apy·(S,S)-1a, apy·(S,S)-1b, apy·(S,S)-2
and apy·(R)-3 in KBr discs. Two of them are presented in Fig. 5.
Experimental
Syntheses of the host compounds
Supplementary Material.
1
–3
are described in
The solid state CD spectra were taken with freshly prepared
KBr disks and recorded with a Jasco J-715 dichrograph. A
mixture of 2–5 mg of the sample and 250 mg of dried KBr was
ground and formed into a disk 0.5 mm thick and with radius of
15 mm. The disk was rotated around the optical axis and the CD
recordings were made for several positions in order to check a
reproducibility of the spectra. The solid state UV-vis spectra
were measured with a Unicam SP-300 spectrophotometer.
Diffraction intensity data were collected on an IPDS 2T dual-
beam diffractometer (STOE & Cie GmbH, Darmstadt, Germany)
at 120.0(2) K with MoKα radiation of a microfocus X-ray source
(GeniX 3D Mo High Flux, Xenocs, Sassenage, 50 kV, 1.0 mA, λ =
0.71069 Å). The investigated crystal was thermostated in
nitrogen stream at 120 K using CryoStream-800 device (Oxford
CryoSystem, UK) during the entire experiment.
Data collection and data reduction were controlled by X-
Area 1.75 program (STOE, 2015). An absorption correction was
performed on the integrated reflections by a combination of
frame scaling, reflection scaling and a spherical absorption
correction. The structures were solved by direct methods and
refined anisotropically using the program packages Olex228 and
SHELX-2015.23b Positions of the C-H hydrogen atoms were
calculated geometrically and taken into account with isotropic
temperature factors. All H-atoms were refined as riding on their
parent atoms with the usual restraints.
Fig. 5. CD (solid line) and UV (dashed line) spectra of apy·(S,S)-1a (blue) and
apy·(R)-3 (red) measured in KBr disks.
Such measurements are possible since the long-wavelength
absorption bands of the azo chromophore remain outside of the
absorption range of the host compounds 1–3. The solid state
UV-vis spectra of the complexes closely resemble that of anti–
azobenzene and are characterized by a weak absorption near
460 nm, corresponding to the forbidden n–π* transition, and a
strong one near 320 nm that can be assigned to the allowed π–
π* transition.27 It has been shown that the positive n–π* Cotton
effect sign can be correlated with the left-handed chirality (M-
helicity) of the skewed aryl-N=N system, and the negative one
with the right-handed chirality (P-helicity).17 Thus the CD
spectrum of apy·(R)-3 featured negative Cotton effect in the
region of the long-wavelength excitation that remains in
accordance with the X-ray structure revealing right-handed
twist of the guest molecule. In the case of apy·(S,S)-1b and
apy·(S,S)-2 (Figure S16 and Figure S17, ESI) the long-wavelength
CD is very weak because the guest molecule is only slightly
twisted from planarity or as in the case of apy·(S,S)-2 assumes
achiral conformation. Instead the weak Cotton effects were
observed near 300 nm in the region of the electronic π–π*
transition, which are caused by external perturbation of the
chromophore by chiral environment created by the host
molecules.
Conclusions
Optically active ditopic halogen bond donors bearing two 4-
iodotetrafluorophenyl groups were successfully obtained by
nucleophilic substitution of iodopentafluorobenzene with chiral
diolate anions. Co-crystallization of these donors with anti-4,4’-
azopyridine afforded binary complexes containing infinite
chains of the alternating component molecules connected by
halogen bonds. These structures are additionally stabilized by
face-to-face π–π stacking interactions between the aryl and
fluoroaryl rings. The complexation of the azopyridine molecule
induces optical activity of the azo chromophore due to the
twisting of the aryl-N=N system or external chiral perturbation
exerted by host molecules, which is manifested by solid state
CD spectra.
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Table 3. Selected crystal data.
apy·(S,S)-1b
C22H16F8I2O4·C10H8N4
934.35
apy·(S,S)-2
C20H14F8I2O2·C10H8N4
876.31
apy·(R)-3
Chemical formula
C32H12F8I2O2·C10H8N4
1018.42
Orthorhombic
P212121
Mr
Crystal system
Space group
Triclinic
P1
Orthorhombic
P212121
a [Å]
b [Å]
c [Å]
α [°]
10.4002 (10)
13.3883 (13)
14.2970 (14)
68.135 (8)
70.540 (8)
69.104 (7)
1679.3 (3)
2
5.2031 (2)
17.8566 (4)
32.8945 (8)
90
11.5438 (5)
14.8242 (7)
21.8290 (17)
90
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β [°]
90
90
90
90
γ [°]
V [Å3]
Z
3056.22 (15)
4
3735.5 (4)
4
Number of measured and
independent reflections
Rint
R[F2 > 2(F2)], wR(F2), S
Flack parameter
CCDC
44176, 17217
38579, 8255
54653, 10101
0.054
0.046, 0.137, 1.07
0.05 (2)
0.047
0.036, 0.091, 1.08
–0.018 (15)
1868142
0.052
0.046, 0.123, 1.09
–0.030 (14)
1868143
1868141
S. Futaki and T. Kawabata, J. Am. Chem. Soc., 2013, 135
,
13644; (c) Z.-X. Xu, Y.-X. Tan, H.-R. Fu, Y. Kanga and J. Zhang,
Chem. Commun., 2015, 51, 2565.
Conflicts of interest
There are no conflicts to declare.
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(a) B. Kesanli and W. Lin, W. Coord. Chem. Rev., 2003, 246,
305; (b) C.-D. Wu and W. Lin, Chem. Commun., 2006, 3673; (c)
C.-D. Wu, A. Hu, L. Zhang and W. Lin, J. Am. Chem. Soc., 2005,
127, 8940.
C. Yang and Y. Inoue, Chem. Soc. Rev., 2014, 43, 4123.
Notes and references
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