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Hydrogen-bonded chains and networks of triptycene-based triboronic acid and tripyridinone Gang Zhang, Frank Rominger, and Michael Mastalerz Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.6b01014 • Publication Date (Web): 05 Aug 2016 Downloaded from http://pubs.acs.org on August 8, 2016

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Crystal Growth & Design

Hydrogen-bonded chains and networks of triptycene-based triboronic acid and tripyridinone Gang Zhang,†,* Frank Rominger, and Michael Mastalerz* Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.

The synthesis of 2,7,14-triptycene triboronic acid 1 and triptycene tripyridinone 2, as well as their packings in the crystalline states were studied. Both compounds show pronounced aggregation by hydrogen bonding, thus forming supramolecular polymeric chains or interpenetrated networks depending on the solvent mixtures used for crystallization. In all examples, two of the three hydrogen bonding motifs in each molecule formed cyclic dimers, leaving the third site either masked by solvents or for the formation of another hydrogen bond with the dimeric units. The influence of the solvent is discussed.

INTRODUCTION Hydrogen bonding, as the most important directional noncovalent interaction force plays a crucial role in biological processes and structure formation as well as in supramolecular chemistry and material science.1,2 Hydrogen bonding motifs are used most frequently in crystal engineering to properly orient molecules in large assemblies to adjust materials properties.3-8 Trimesic acid for instance can form hexagonal networks due to its regular D3h-symmetry and the

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possible formation of cyclic hydrogen bonding dimers of the carboxylic acid units.9-11 Crystal engineering of larger molecules assembling via hydrogen bonding were really pushed forward by Wuest et al., who initially studied the aggregation of adamantoid pyridinone-anchored molecular tectons into diamondoid network forming nanoporous chambers.12 In addition to pyridinone,13-16 other hydrogen bonding motifs, such as diaminotriazinyl (DAT),17-25 phenol,26,27 boronic acid,28,29 were also investigated. All of these molecular tectons led to the formation of organic solids with large solvate-filled pores in the crystalline states. Wuest concluded in one of his early papers that the strategy of molecular tectonics would lead to construct materials with useful properties.12 Indeed, porous organic hydrogen-bonding frameworks have been used or gas storage and separation, enantioselective separation of chiral compounds.30-43 Although hydrogen bonding interactions have been studied for many years, the prediction of the packing of the molecules in crystal lattice is still a very challenging task and the role of the used solvents is still not understood.44-46 For example, crystallization of melamine from different solvents could change the directions of hydrogen bonding in solid state leading to the formation of a porous or a non-porous material.47,48 Triptycene, as a rigid three-dimensional D3h-symmetric molecule, has been proved to be a versatile building block in the realm of materials science,49-51 especially for porous compounds due to the large internal molecular free volume originated from its unique shape.52-69 As far as crystal engineering is concerned, triptycene is also an ideal scaffold to study the molecular packing in the solid state due to its directionality and ease of functional derivatization. Recently, Chen et al. and MacLachlan et al. investigated the interaction of triptycene based phenols and catechols with bipyridine and quaternary ammonium bromide via hydrogen bonding in solid state.70-73 An interesting result is the formation of hexagonal nanotubes via OH--Br interaction,


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in spite of partially oxidization of catechol to quinone units. Our group introduced triptycene trisbenzimidazolones, which self-assemble via hydrogen bonding to generate a porous organic crystal with one-dimensional channels and an extraordinarily high specific surface area of 2796 m2/g.74 As aforementioned, boronic acid and pyridinone units are reliable hydrogen bond forming groups. Here we report the crystal structure packing of two new C3v symmetrical 2,7,14triptycene triboronic acid 1 and triptycene tripyridinone 2 (Scheme 1) by hydrogen bonding interactions of crystals derived from various solvents.

Scheme 1. Structures of 2,7,14-triptycene triboronic acid 1 and tripyridinone 2. RESULTS AND DISCUSSION The synthesis of 2,7,14-Triptycene triboronic acid 1 started with a Miyaura borylation of 2,7,14-tribromotriptycene75 and subsequent oxidation of the intermediate boronic ester with NaIO4 in 48% yield for two steps. The trispyridonyltriptycene 2 was obtained in 57% yield by a Suzuki-Miyaura cross-coupling reaction of the intermediate pinacol boronic ester with 3-bromo6-phenylmethoxypyridine, followed by deprotection of the benzyl groups via hydrogenation over 5% Pd/C (see Supporting Information). Crystals of triboronic acid 1 were obtained by


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recrystallization from water. The crystallization of 2 were carried out in various carboxylic acids as solvents or DMSO together with methanol and/or hexane. Crystal data are listed in Table 1. Table 1 Crystal data of 1 and 2.

Crystallization solvents Empirical formula Formula weight Temperature (K) Wavelength (Å) Crystal system Space group Z a (Å) b (Å) c (Å) α ( deg.) β ( deg.) γ ( deg.) Volume (Å3) Dcalculated (g/cm3) µ (mm−1) Crystal shape Crystal size (mm) Crystal colour θ range (deg.) Index ranges

Reflections collected Independent reflections Observed reflections GOF on F2 Final R indices (I>2σ (I)) Largest diff. Peak/hole (eÅ-3)

Crystal 1 water C20H17B3O6 385.76 200(2) 0.71073 monoclinic C2/c 8 23.412(2) 11.2486(12) 22.232(3) 90 120.767(3) 90 5030.8(11) 1.02 0.07 plate 0.22 × 0.08 × 0.02 colourless 2.0-25.0 -27≤ h ≤27 -13≤ k ≤13, -26≤ l ≤26 15695 4463 (R(int) = 0.0745) 2556 (I > 2σ(I)) 1.04 R1 = 0.076, wR2 = 0.191 0.78/-0.70

Crystal 2a propionic acid/ hexane C48.50H51N3O10.50 843.92 200(2) 0.71073 triclinic Pī 4 11.695(4) 15.732(5) 25.759(8) 106.989(8) 92.567(9) 90.995(9) 4526(2) 1.24 0.09 polyhedron 0.11 × 0.10 × 0.08 colourless 1.4-19.6 -11≤ h ≤11 -14≤ k ≤14 -24≤ l ≤24 20627 7951 (R(int) = 0.1054) 3861 (I > 2σ(I)) 1.04 R1 = 0.101 wR2 = 0.255 0.74/-0.37

Crystal 2b valeric acid/ MeOH /hexane C39H34N3O4 608.69 200(2) 0.71073 monoclinic P21/c 4 10.4426(17) 14.301(2) 21.049(3) 90 91.010(5) 90 3143.0(9) 1.29 0.08 polyhedron 0.13 × 0.11 × 0.09 colourless 1.7-25.0 -12≤ h ≤12 -15≤ k ≤17 -25≤ l ≤25 29357 5541 (R(int) = 0.0479) 4083 (I > 2σ(I)) 1.03 R1 = 0.058 wR2 = 0.133 0.43/-0.28

Crystal 2c DMSO/MeOH C37H31N3O5 597.65 200(2) 0.71073 orthorhombic Pca21 4 26.628(2) 12.1545(9) Å 9.0915(7) Å 90 90 90 2942.5(4) 1.35 0.09 needle 0.21×0.06× 0.05 colourless 1.5-25.1 -31≤h≤31 -14≤k≤14 -10≤l≤10 22708 5165 (R(int) = 0.0557) 3990 (I > 2σ(I)) 1.06 R1 = 0.058, wR2 = 0.142 0.58/-0.23

Crystal structure of triboronic acid 1. The monoclinic unit cell contains eight molecules of triptycene triboronic acid 1 and fifty-six molecules of water. It is known that boronic acids can form cyclic hydrogen-bonded dimers,44-46,76-78 similar to that found in the carboxylic acid dimer,79 and in most cases the two hydroxyl groups prefer the syn-anti conformations according to the H-atom locations (Scheme 2, type I).80 However, the three boronic groups of 1 play


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different roles in the formation of hydrogen bonds: two boronic groups form cyclic hydrogenbonded dimer with both hydroxyls on one boronic acid as donor and the other one as acceptor in the way of syn-syn and anti-anti (type II); the third one with a conformation of syn-syn renders with one of the two hydroxyls groups to form a hydrogen bond with the oxygen atom of the aforementioned hydrogen bond donor site. The presence of the third hydrogen bond influences the two hydrogen bonds of the cyclic dimer, which is weakening one bond and thus becoming different in lengths (d(O(11)--O(31)) = 2.748 Å and d(O(12)--O(32)) = 2.701 Å (Table 2). The values of the in the same dimeric unit O–B–O angles are also different, with ∠(O11–B–O12) = 121°, ∠(O21–B–O22) = 121° and ∠(O31–B–O32) = 114°. The boronic group with a syn-syn arrangement gives a bigger O–B–O angle than the boronic group in the anti-anti conformation, which is probably caused by the repulsion of H--H contacts.80 The value of the O–B–O angle in type I bonding is in the range of 116° to 120°, just between the angles in type II bonding.44 The dihedral angles of the planes defined by the phenyl ring and its connected boronic acid moieties are 34°, 28° and 6°, respectively, showing the flexibility of the boronic group.81 The two relatively big angles are reasonable considering the steric hindrances caused by outward pointing hydroxyls with the neighboring hydrogen atoms of the phenyl ring and the formation of hydrogen bonding between O(11) and O(22). With the aid of these three hydrogen bondings, the triboronic acids self-assembled into two-dimensional porous molecular layer with a pore size of 1.59 nm. However, the pore size is so large that another independent molecular layer is allowed to interpenetrate giving an interlaced networks (Figure 1b).82


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H O Ar B O

H H

syn-anti type I

O B Ar O H

H O Ar B O H anti-anti

H

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O B Ar O

H

syn-syn type II

Scheme 2. Hydrogen bonding interactions between two molecules of boronic acid.

Figure 1. Representations of the structure of crystals of 1. (a) Representative H-bonding among boronic acids found in the crystalline state. (b) Two layers of networks that interweave to form lattice-like structure viewed along c axis with the water molecules omitted for clarity. (c) Interactions of water molecules and triboronic acid molecules. Colour code in (a) and (c): gray, carbon; white, hydrogen; yellow, boron; red, oxygen.


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A large number of solvent water was confined in the crystal lattice during crystal growth. The two-dimensional networks were brought together through water bridges containing one or six water molecules to generate a complex three-dimensional framework. For the water bridge bearing six water molecules, a four-member ring was formed with the other two molecules of water (W7) located above and below the ring by forming the hydrogen bonding with the same oxygen atom (W6) as the acceptor. The O--O distances between these six water molecules are 2.873 Å (O(W1)--O(W5)), 2.849 Å (O(W1)--O(W6)) and 2.784 Å (O(W6)--O(W7)). For comparison, the O--O separations in ice Ih (T = 223 K) and liquid water are 2.76 and 2.85 Å,83 respectively. The bond angles of O--O--O varied from 76° (O(W7)--O(W6)--O(W7)) to 137° (O(W1)--O(W6)--O(W7)) with a deviation up to 33° from the ideal tetrahedral angle found in ice Ih (T = 223 K).83 These hydrogen-bonded water molecules could not be regarded as enclathrated ice according to the ice rule, that each water molecule should have four hydrogen bonded neighbors,84 which is not present in this case. Crystal structure of tripyridinone 2. Several different solvent systems were attempted for crystallization of trispyridinone 2, however, crystals suitable for X-ray analysis were only obtained from three different crystallization media. These three types of crystals possess different space groups but all bearing four molecules in each unit cell. From propionic acid/hexane, the compound crystallized in the triclinic space group Pī (solvate 2a) with another four molecules of hexane and sixteen molecules of propionic acid in a unit cell. Hydrogen bonds are formed between two of the three pyridinones in 2 to give two kinds of polymer chains that propagate in the c direction and the bc-diagonal direction. The two hydrogen bonds in the same cyclic hydrogen bonding rings share a uniform distance. But each of these two polymer chains possesses two different hydrogen bonding distances even in the same chains, 2.762 Å and 2.792


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Å (N--O distance in chains of c direction) (Table 2), 2.804 Å and 2.822 Å (N--O distance in chains of bc-diagonal direction), which were alternated along each chains. The two chains have a crossing point where they are in π-contact with an average distance of 3.320 Å. The angles of N–H--O are between 169° and 175° with the dihedral angles of the phenyl ring and pyridinone ring in the range from 26° to 39° due to the rotatable single bond that connecting them. The propionic acid solvate molecules have dual role, either they are masking the third pyridonyl group of 2 as a cyclic heterodimer (Figure 2c) prevented the further extension of 2 to another direction, thus only resulting in the formation of one-dimensional chains. The second type of propionic acid molecules found, acting as hydrogen bond donors interacting with the oxygens of the pyridonyl units in their homodimers. Furthermore enclathrated hexane and water molecules have been found.


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Figure 2. Representations of the structure of crystals of 2a obtained from propionic acid/hexane. (a) Formation of one-dimensional polymer via H-bonding among pyridonyls on triptycene. (b) Two polymer chains that cross each other, the red one in the bc-diagonal direction and the blue one in the c direction. (c) Propionic acid molecules that append to each pyridonyl part. Colour code in (a) and (c): gray, carbon; white, hydrogen; light blue, nitrogen; red, oxygen. Crystal 2b was obtained by slow vapor diffusion of hexane into a methanol/valeric acid solution of 2. The crystal is monoclinic with a P21/c space group having four molecules of methanol and two molecules of hexane in a unit cell. In contrast to crystal 2a, no valeric acid molecules were found binding to the pyridonyl units. Cyclic hydrogen bonding rings formed between two of the three pyridonyl functions to furnish a zigzag chain with alternated N--O distances of 2.758 Å and 2.831 Å, respectively (Figure 3a). The NH of a third pyridonyl unit interacts with the carbonyl-O of a pyridonyl moiety already involved in a cyclic hydrogen bonding ring, by another hydrogen bond (N--O distance 2.912 Å). Furthermore, methanol is bound to this third pyridinone via hydrogen bonding to the carbonyl-O. Compared with the other two N--O distances in the crystal, this N--O distance is longer, accompanied with a smaller N–H-O angle of 156°, which can in turn be interpreted by the additional binding of methanol molecule causing a distortion. The two pyridinones that form the cyclic hydrogen bonding ring without additional bonding nearby are coplanar without deviation. However, in another cyclic hydrogen bonding ring, the two pyridonyl rings slightly deviate from planarity with a dihedral angle of 2°. Furthermore, these two additional interactions weaken the hydrogen bonding within the cyclic ring, which was reflected by a little longer N--O distance (2.831 Å). The dihedral angles of the phenyl ring and pyridinone plane in 2 are 22°, 23° and 43°, respectively.


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With the aid of these hydrogen bonding interactions, a three-dimensional supramolecular framework is generated with an interpenetrated compact architecture (Figure 3b), similar to the network of 1. Interestingly, hexane molecules were enclathrated inside the cavities amongst the supramolecular assembly.

Figure

3.

Representations

of

the

structure

of

crystals

of

2b

obtained

from

methanol/hexane/valeric acid. (a) Representative H-bonding among pyridonyls on triptycene. (b) Formation of interpenetrated compact supramolecular framework. (c) A hexane molecule (spacefilling model) trapped inside the cavity. Colour code in (a) and (c): gray, carbon; white, hydrogen; light blue, nitrogen; red, oxygen.


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Crystal 2c was obtained by slowly vapor diffusion of methanol into a DMSO solution of 2. The compound crystallized in the orthorhombic space group Pca21 including eight molecules of methanol in a unit cell. In this crystal each pyridonyl unit is arranged in a trimeric hydrogen bonding pattern, where two closer pyridonyl rings form a cyclic dimer, which deviates from planarity with a dihedral angle of 45°, and small N–H--O angles (148° and 160°). The N--O distances within the cyclic interactions are not identical (3.008 Å and 2.763 Å, respectively) (Figure 4a). N–H from another pyridonyl motif binds to the carbonyl (O64) with a N--O distance of 2.768 Å, close to the N--O distance that shares the same oxygen atom (O64). The planar deviation of the two pyridonyl rings as well as the difference in the N--O distances within the hydrogen bonding cyclic ring are caused by the interaction of the third pyridonyl group, which renders the O44--H52–C contact (O--H distance 2.411 Å) making the pyridonyl ring (N53) in close proximity to the adjacent pyridonyl ring (N43). The dihedral angles of the pyridonyl plane and the adjacent phenyl ring are 18°, 40° and 46°, respectively. Methanol molecules are found attached to pyridinone via hydrogen bonding, but no DMSO was connected due to its relatively weak association ability. With the assistance of the acyclic hydrogen bond, a three-dimensional supramolecular porous hierarchical framework is formed. However, two frameworks generate an interlocked compact supramolecular structure with one-dimensional channels once viewed along c axis (Figure 4b). The void space is 9.6% if a probe radius of 1.8 Å is assumed. However, any attempts to remove enclathrated solvent from the pores were not successful to date to create a microporous material. Since the diameter of the pores is about 7.0-7.2 Å, a permanent porous material would be interesting for methane adsorption.85


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Figure 4. Representations of the structure of crystals of 2c obtained from methanol/DMSO. (a) Representative H-bonding among pyridonyls on triptycene. (b) Formation of interpenetrated compact supramolecular framework with one-dimensional channels viewed along c axis. Colour code in (a): gray, carbon; white, hydrogen; light blue, nitrogen; red, oxygen. Table 2. Summary of hydrogen bonding interaction details and geometries revealed in these four crystals. D–H

H--A

D–H--A D–H--A

(Å)

(Å)

(Å)

donor–H--acceptor 1

angle (deg.)

O12–H12--O32

0.945 1.776 2.701

166

O11–H11--O31

0.954 1.803 2.748

171


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O22–H22--O11

0.955 1.756 2.706

173

2a N53–H53--O54 (c)

0.88

1.885 2.762

174

N63–H63--O64 (c)

0.88

1.923 2.792

169

N43–H43--O44 (bc) 0.88

1.945 2.822

174

N63–H63--O64 (bc) 0.88

1.926 2.804

175

2b N65–H65--O64

0.88

1.880 2.758

175

N45–H45--O44

0.88

1.969 2.813

160

N25–H25--O44

0.88

2.085 2.912

156

N63–H63--O54

0.88

2.225 3.008

148

N53–H53--O64

0.88

1.919 2.763

160

N43–H43--O64

0.88

1.903 2.768

167

2c

CONCLUSIONS In summary the single crystal X-ray structure analyses reveal the formation of solvent-depended supramolecular polymer chains and interpenetrated networks from discrete triptycene triboronic acid and tripyridone molecules via O–H--H and N–H--O hydrogen bonding interactions. For both boronic acid 1 and pyridinone 2 typically two cyclic dimers have been formed, whereas the third unit either got masked by solvents or located beside the cyclic dimer via single hydrogen bonding force, which prohibits the formation of a three dimensional framework but yields one dimensional chain and two dimensional networks. When DMSO is used with methanol, a three dimensional interpenetrated porous network is formed that might potentially being desolvated. Up to now, we haven’t found any other solvate structures, but the influence of larger solvent molecules on the resulting crystals is under investigation. Furthermore, one can conclude, that the degrees of freedom by the rotatable single bond that is linking boronic acid or pyridinone units with the triptycene scaffold increases the possibilities of the directions of the formed


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hydrogen bonds, making the organization of the molecules even more complicated and hard to predict the resulting structure. Because the pyridinone unit is one of the most reliable hydrogen bonding motif, usually forming dimeric units, we are currently interested in placing those on a more rigid triptycene scaffold.86 ASSOCIATED CONTENT Supporting Information. Further details of synthesis and characterization. CCDC 14836831483686. This material is available free of charge via the Internet at http://pubs.acs.org. AUTHOR INFORMATION Corresponding Author * [email protected] *[email protected] Present Addresses † College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing, P. R. China. Notes The authors declare no competing financial interest. ACKNOWLEDGMENT The authors would like to thank the Ruprecht-Karls-Universität for financial support in the frame of excellence intitative II. Furthemore, G.Z. is grateful for a postdoctoral fellowship of the Alexander-von-Humboldt foundation.


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“For Table of Contents Use Only ” Manuscript title: Hydrogen-bonded chains and networks of triptycene-based triboronic acid and tripyridinone Author list: Gang Zhang, Frank Rominger, and Michael Mastalerz TOC Graphic

Synopsis The hydrogen bonding aggregation of C3v symmetrical 2,7,14-triptycene triboronic acid and triptycene tripyridinone revealed the formation of supramolecular polymer chains and interpenetrated networks in their crystalline states.


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Hydrogen-Bonded Chains and Networks of ... - ACS Publications

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