Solution and Mechanochemical Syntheses of Two Novel Cocrystals

Article pubs.acs.org/crystal

Solution and Mechanochemical Syntheses of Two Novel Cocrystals: Ligand Length Modulated Interpenetration of Hydrogen-Bonded 2D 63‑hcb Networks Based on a Robust Trimeric Heterosynthon Lu-Lu Han,†,‡ Zhong-Hui Li,† Jiang-Shan Chen,† Xing-Po Wang,† and Di Sun*,† †

Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People’s Republic of China ‡ State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, People’s Republic of China S Supporting Information *

ABSTRACT: Cocrystallization of a versatile organic tecton, 3,3′,5,5′-tetramethyl-4,4′-bipyrazole (tmbpz), with aliphatic dicarboxylic acid suberic acid (H2sub) and sebacic acid (H2seb) generates two supramolecular solids [(tmbpz)2·(H2sub)] (1) and [(tmbpz)2·(H2seb)] (2). In the present case, both cocrystals could be obtained from either solution evaporation or mechanochemical solid-state reaction. Single-crystal structural analyses reveal that the 1 and 2 are 4-fold and 5-fold 2D → 2D parallel interpenetrated 63-hcb networks, respectively. The substantial dissimilarities in the degree of interpenetration are modulated by the different lengths of dicarboxylic acids. The thermal stabilities and photoluminescence behaviors of them were also discussed.

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INTRODUCTION

example of the construction of interpenetrating hydrogenbonded networks was a 2:3 cocrystal of trimesic acid and 1,2bis(4-pyridyl)ethane made by Shattock et al.5 This 2:3 cocrystal system always exhibits concomitant polymorphism, a common 3-fold 2D → 2D parallel interpenetrated 63-hcb net and a record of 18-fold interpenetrated 103-a net. Although two isomers contain the same carboxylic acid−pyridine supramolecular heterosynthons, a conformational difference between the 1,2-bis(4-pyridyl)ethane in two crystal forms influences the linkage orientation, thus extending the three-connected trimesic acid to the networks with different topologies and interpenetration degrees. The investigation on interpenetrated systems advanced rapidly, but predicting and control of interpenetration, especially in hydrogen-bonding directed organic networks, remains a long-standing challenge, and only sporadic examples appeared.6 Thus, accurately controlling the

The design and construction of entangled networks, in which molecules are intertwined with each other and could not be isolated as a single network without breaking links, have captivated the attention of many investigators in crystal engineering and supramolecular chemistry for both aesthetic and practical application reasons.1 Interpenetrated structures constitute a subgroup within a broader class of entangled systems, which are very common in coordination polymers and many advances have been witnessed in developing strategies for synthesizing metal−organic architectures with controllable interpenetrated topologies.2 Compared with the widely reported interpenetrated metal-containing infinite networks, there are few instances involving entangled hydrogen-bonded networks,3 which remain one of the foremost challenges in the crystal engineering of molecular solids due to an elusive linking mode between the supramolecular synthons. One of the most famous hydrogen-bonded interpenetrated networks was an elongated 5-fold diamond structure based on tetrahedral adamantane-1,3,5,7-tetracarboxylic acid.4 Another remarkable © 2014 American Chemical Society

Received: November 20, 2013 Revised: January 22, 2014 Published: January 24, 2014 1221

dx.doi.org/10.1021/cg4017454 | Cryst. Growth Des. 2014, 14, 1221−1226

Crystal Growth & Design

Article

spectrometer at the range of 4000−400 cm−1. Elemental analyses were carried out on a CE instruments EA 1110 elemental analyzer. Photoluminescence spectra were measured on a Hitachi F-7000 fluorescence spectrophotometer (slit width, 5 nm; sensitivity, high). Xray powder diffractions were measured on a Panalytical X-Pert pro diffractometer with Cu Kα radiation. Thermogravimetic analyses were performed on a NETZSCH TG 209 F1 Iris thermogravimetric analyzer from 30 to 800 °C at a heating rate 10 °C/min under the N2 atmosphere (20 mL/min). Solution Preparation of Complexes 1 and 2. [(tmbpz)2· (H2sub)] (1). Reaction of H2sub (34 mg, 0.2 mmol) and tmbpz (38 mg, 0.2 mmol) in methanol−water mixed solvent (6 mL, v/v: 1/1) was performed under ultrasonic treatment. The resultant colorless solution was allowed slowly to evaporate at room temperature for 3 weeks to give yellow block crystals of 1. (yield: 62%). They were washed with a small volume of cold CH3OH and diethyl ether. Anal. Calcd for C14H21N4O2: C 60.63, H 7.63, N 20.20%. Found: C 60.22, H 7.21, N 20.39%. Selected IR peaks (cm−1): 3048 (w), 2911 (w), 2862 (w), 1572 (s), 1425 (m), 1388 (s), 1310 (s), 1211 (m), 1072 (w), 999 (w), 845 (m), 630 (w), 516 (w). [(tmbpz)2·(H2seb)] (2). Synthesis of 2 was similar to that of 1, but using H2seb (44 mg, 0.2 mmol) instead of H2sub. Pale-yellow crystals of 2 were obtained in 46% yield. Anal. Calcd For C15H23N4O2: C 61.83, H 7.96, N 19.23%. Found: C 61.72, H 8.06, N 19.56%. Selected IR peaks (cm−1): 3160 (w), 2911 (w), 2825 (w), 1537 (s), 1441(s), 1376 (s), 1321 (w), 1265 (w), 1065 (m), 988 (w), 914 (w), 605 (m). Solid-State Synthesis. In the solid-state reactions tmbpz and H2sub or H2seb were manually ground together in an agate mortar in 1:1 molar ratio for ca. 30 min. A few drops of methanol were added to the grinding mixture. Formation of the solid products 1 and 2 was confirmed by comparison of the experimental XRPD patterns with those calculated on the basis of single crystals of the corresponding compounds prepared by conventional solution crystallization as described above. X-ray Crystallography. Single crystals of the complexes 1 and 2 with appropriate dimensions were chosen under an optical microscope and quickly coated with high vacuum grease (Dow Corning Corporation) before being mounted on a glass fiber for data collection. Data for them were collected on a Bruker Apex II CCD diffractometer with graphite-monochromated Mo Kα radiation source (λ = 0.71073 Å). A preliminary orientation matrix and unit cell parameters were determined from 3 runs of 12 frames each, each frame corresponds to a 0.5° scan in 5 s, followed by spot integration and least-squares refinement. For 1 and 2, data were measured using ω scans of 0.5° per frame for 10 s until a complete hemisphere had been collected. Cell parameters were retrieved using SMART software and refined with SAINT on all observed reflections.15 Data reduction was performed with the SAINT software and corrected for Lorentz and polarization effects. Absorption corrections were applied with the program SADABS.15 In all cases, the highest possible space group was chosen. All structures were solved by direct methods using SHELXS9716 and refined on F2 by full-matrix least-squares procedures with SHELXL-97.17 Atoms were located from iterative examination of difference F-maps following least-squares refinements of the earlier models. Hydrogen atoms were placed in calculated positions and included as riding atoms with isotropic displacement parameters 1.2− 1.5 times Ueq of the attached C atoms. All structures were examined using the Addsym subroutine of PLATON18a to ensure that no additional symmetry could be applied to the models. Pertinent crystallographic data collection and refinement parameters are collated in Table 1. The hydrogen bond geometries are collated in Table 2. Their interpenetration modes were analyzed with the program TOPOS.18b

interpenetration degree of the same topology of hydrogenbonded network by length of organic tecton deserved to be studied. As a versatile molecular tecton, 3,3′,5,5′-tetramethyl-4,4′bipyrazole (tmbpz) has been widely used for construction of solid state hydrogen-bonded and coordination arrays,7 because (i) it could adopt different coordination conformations arising from the nearly unhindered torsion of the pyrazole rings along the single bond between the rings, (ii) it also has a pair of selfcomplementary hydrogen-bond donor (NH) and acceptor (N) sites for the formation of a hydrogen-bonded network, and (iii) the pyrazole moieties readily give coordination compounds with metal ions in neutral as well as in mono- or dianionic forms. Although tmbpz−phenol cocrystals have been reported by the Domasevitch group,8 tmbpz−dicarboxylate cocrystals are still in their infancy. Mechanochemical reactions are environmentally beneficial and occur when reactants are mixed together in the solid state, which has emerged as an excellent experimental method to rapidly and efficiently synthesize organic compounds, 9 cocrystals,10 and coordination networks11 by simple manual grinding or mechanical milling.12 It is becoming more intensely studied partly because it can promote reactions between solids quickly and quantitatively, with either no added solvent or only nominal amounts. Within this context, cocrystal synthesis by grinding has proven superior to the more traditional method of synthesis from solution. Mechanochemical synthesis of cocrystals using grinding has been reviewed by the Braga group,13 and the mechanistic aspects were also discussed by Jones and co-workers.14 On the basis of these considerations, using aliphatic dicarboxylic acids as one of cocrystallization components, we obtained two binary tmbpz−dicarboxylate cocrystals, [(tmbpz)2·(H2sub)] (1) and [(tmbpz)2·(H2seb)] (2) (tmbpz = 3,3′,5,5′-tetramethyl-4,4′-bipyrazole, H2sub = suberic acid, and H2seb = sebacic acid; Scheme 1), which show 4-fold and 5Scheme 1. Supramolecular Heterosynthons and Organic Components for Cocrystallization

fold 2D → 2D parallel interpenetrated 63-hcb networks, respectively, depending on the lengths of dicarboxylic acids. The “green” mechanochemical reaction route was also proven to be efficient in the synthesis of 1 and 2.

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RESULTS AND DISCUSSION

Structure Descriptions. [(tmbpz)2·(H2sub)] (1). X-ray single-crystal diffraction analysis reveals that 1 is a 4-fold 2D → 2D parallel interpenetrated 63-hcb network. It crystallizes in the orthorhombic crystal system with space group of Pbcn. The

EXPERIMENTAL SECTION

Materials and General Methods. Chemicals and solvents used in the syntheses were of analytical grade and used without further purification. IR spectra were measured on a Nicolet 330 FTIR 1222



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Table 1. Crystal Data for 1 and 2 complex empirical formula formula weight temp, K cryst syst space group a, Å b, Å c, Å α, deg β, deg γ, deg vol, Å3 Z ρcalc (mg/mm3) μ/mm−1 F(000) reflns collected independent reflns data/restraints/params goodness-of-fit on F2 final R indexes [I ≥ 2σ(I)] final R indexes [all data] largest diff. peak/hole/e Å−3

1 C14H21N4O2 277.35 298(2) orthorhombic Pbcn 22.389(3) 8.2386(11) 16.762(14) 90.00 90.00 90.00 3092(3) 8 1.192 0.082 1192.0 14 587 2717 2717/1/186 1.057 R1 = 0.0678, wR2 = 0.1808 R1 = 0.1231, wR2 = 0.2178 0.26/−0.26

2 C15H23N4O2 291.37 298(2) orthorhombic Pbca 7.5238(9) 16.626(2) 26.574(3) 90.00 90.00 90.00 3324.2(7) 8 1.164 0.079 1256.0 14 051 2906 2906/0/195 1.037 R1 = 0.0656, wR2 = 0.1553 R1 = 0.1210, wR2 = 0.1830 0.19/−0.20

Figure 1. (a) The supramolecular heterosynthons in 1 with the thermal ellipsoids at 30% probability level (symmetry codes: (i) x, −y + 2, z − 1/2; (iii) −x + 1, −y + 1, −z + 1). (b) The hexagon in the 63hcb network based on triangular trimeric heterosython I and mixed linear linkers. (c) Side view of 4-fold 2D → 2D parallel interpenetrated 63-hcb networks. (d) One red hexagonal window threaded by three other windows. (e) Simplified 4-fold 2D → 2D parallel interpenetrated 63-hcb networks (networks individually colored).

Table 2. The Hydrogen Bond Geometries (Å and deg) for 1 and 2 DH···A N2H2···N4ii N3H3···O1iii O2H2A···N1iv N1H1···O2ii N3H3···N2iii O1H1D···N4iv

DH

H···A

Complex 1a 0.86 2.02 0.86 1.85 0.82 1.99 Complex 2b 0.86 1.98 0.86 2.04 0.82 1.98

D···A

DH···A

2.824(4) 2.700(4) 2.659(4)

155 171 138

2.819(4) 2.842(4) 2.699(3)

164 155 145

platonic uniform net and can be represented by the symbol (n,p), where n is the size of the shortest circuit and p is the connectivity of the nodes.22 In 1, all heterosythons I are threeconnecting, and the shortest circuit is a six-membered ring. So a wavy honeycomb layer stabilized by heterosython I is formed, and topologically, this layer is a 63-hcb network (Figure 1b), which incorporates a hexagonal window with the dimension of 23.26 × 20.00 Å2 defined by the lengths of two diagonals. As a consequence of Mother Nature’s horror vacui, such a large window is simultaneously threaded by three other identical hydrogen-bonded windows (Figure 1d) resulting in the 4-fold parallel interpenetrated network (Figure 1c,e). [(tmbpz)2·(H2seb)] (2). When a longer H2seb was used as one of the cocrystallization components, a much higher degree of interpenetration was observed. Complex 2 is a 5-fold 2D → 2D parallel interpenetrated 63-hcb network. It crystallizes in the orthorhombic crystal system with space group of Pbca. The asymmetric unit contains one tmbpz and a half of H2seb sitting on the inversion center. In the crystal structure of 2, both tmbpz and H2seb are also neutral and no proton transfer between them is observed. The similar triangular trimeric heterosython I comprised of two tmbpz and one H2seb is observed in 2 with the N−H···N, N−H···O, and O−H···N hydrogen bonds being 2.819(4), 2.842(4), and 2.699(3) Å, respectively. Two pyrazolyl rings of the tmbpz are nearly perpendicular to each other with the interplanar angle ϕ of 82.59(19)°. The H2seb possesses a ten carbon aliphatic backbone, and there exist seven torsion angles; hence, the conformation of H2seb molecule is anti-anti-anti-anti-anti-antianti defined by seven torsion angles along the C chain of 171.1(3)°, 176.6(3)°, 178.8(3)°, 180°, 178.8(3)°, 176.6(3)°, and 171.1(3)°. Using a similar simplification procedure, the network of 2 is also a 63-hcb network. The window dimension

a Symmetry codes: (ii) x, −y + 2, z + 1/2; (iii) −x + 1, −y + 1, −z + 1; (iv) −x + 1, y − 1, −z + 3/2. bSymmetry codes: (ii) −x + 3/2, y − 1/ 2, z; (iii) −x + 1/2, y + 1/2, z; (iv) x + 1, y, z.

asymmetric unit contains one tmbpz and a half of H2sub sitting on the inversion center. In the crystal structure of 1, both tmbpz and H2sub are neutral and no proton transfer between them occurs. The tmbpz and H2sub act as single hydrogen bond donor and acceptor to form one triangular trimeric heterosython I (Figure 1a) through one N−H···N (2.824(4) Å), one N−H···O (2.700(4) Å), and one O−H···N (2.659(4) Å) hydrogen bond. The heterosython19 I belongs to an R33(10) motif according to graphset analysis nomenclature.20 The interplanar angle ϕ determined by two pyrazolyl rings of the tmbpz is 68.2(2)°. The H2sub possesses an eight -carbon aliphatic backbone, and there exist five torsion angles; hence, the conformation of the H2sub molecule is anti-anti-anti-antianti defined by five torsion angles along the C chain of 177.7(4)°, 178.6(4)°, 180°, 178.6(4)°, and 177.7(4)°.21 To better understand the hydrogen-bonded structure of 1, the topological analysis approach is employed. If all nodes in one net have identical connectivity, then according to Wells it is a 1223



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in 2 (25.19 × 21.49 Å2) is much larger than that in 1; as a result, four identical networks thread the same hexagonal window, generating a 5-fold parallel interpenetrated network (Figure 2). For supramolecular cocrystals, some interpenetrated

resulting structure unchanged, which facilitates investigation of the correlation of degree of interpenetration with length of tecton. In 1 and 2, the tmbpz ligand has a fixed length, and heterosython I keeps its nature of three-connected node, but H2sub and H2seb tectons have obviously different lengths of 10.6 and 13.6 Å, respectively; as a consequence, similar 2D networks with identical three-connected 63-hcb topology but incorporating a different size of void space were obtained. The larger the void space is, the more equivalent networks can be accommodated, so a higher degree of interpenetration was formed. The results described herein provide an indication that simple but efficient ways to control interpenetration degree of the same topology in hydrogen-bonded organic networks are at hand. Mechanochemical Synthesis, PXRD Results, and Thermal Analysis. To explore the feasibility of mechanochemical synthesis in this system, we performed a solid-state reaction by manual grinding in an agate mortar of equimolar quantities of the two solid materials. In order for the reaction to take place, several drops of MeOH was added during work-up, and the grinding was performed for 30 min. After grinding, the powder products obtained by this method were dried by standing in air. Our characterization approach is based on comparison of PXRD patterns of the products obtained directly by grinding with those obtained by crystallization from solution. Based on the obtained single crystals, these can be used to determine the solid-state structure in detail and, in turn, to calculate the reference powder diffractogram. Comparison of the calculated diffractogram with that measured from the mechanochemical product allows one to establish with confidence whether the same phase or a different one or a mixture of phases has been obtained. The comparative PXRD patterns are shown in Figure 3. They show that the synthesized bulk single crystalline materials and the measured single crystals are the same and the PXRD patterns of samples from mechanochemical synthesis are also identical to those from the measured single crystals, proving the efficiency of mechanochemical synthesis in this system. The thermogravimetric (TG) measurements were performed in a N2 atmosphere on polycrystalline samples of complexes 1 and 2 and the TG curves are shown in Figure S1, Supporting Information. The TGA curves of 1 and 2 show similar thermal stability, and the complexes can be stable to ca. 176 °C; then the organic components were burned out at ca. 500 °C. Photoluminescence Properties. The H2sub and H2seb were emission silent at room temperature. The photoluminescent spectra of cocrystals 1 and 2 were measured at 298 and 77 K (Figure 4). Under excitation at 300 nm, the maximum emissive peak of 1 was located at 466 nm at 298 K; when 1 was cooled to 77 K, no obvious emission shift occurred, but the emission intensity was enhanced compared with that at 298 K. The emission maximum of 2 was located at 469 nm at 298 K; when 2 was cooled to 77 K, the emission peak blueshifted to 461 nm, accompanying the enhanced intensity. Compared with the emission peak of free tmbpz (λmax = 480 nm),28 blue-shifted emissions of cocrystals 1 and 2 were observed, which suggested that the formation of the robust hydrogen-bonded heterosython I and interpenetrated network structures may (i) change the energy levels of their highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) and (ii) effectively increase the rigidity of them in crystal packing and reduce the loss of energy by radiationless decay; as a consequence, the emissions of the

Figure 2. (a) The supramolecular heterosynthons in 2 with the thermal ellipsoids at 30% probability level (symmetry codes: (i) −x + 5/2, y − 1/2, z; (ii) −x + 3/2, y − 1/2, z; (iv) x + 1, y, z). (b) The hexagon in the 63-hcb network based on triangular trimeric heterosython I and mixed linear linkers. (c) Side view of 5-fold 2D → 2D parallel interpenetrated 63-hcb networks. (d) One red hexagonal window threaded by four other windows. (e) Simplified 5-fold 2D → 2D parallel interpenetrated 63-hcb networks (networks individually colored).

63-hcb networks have been documented based on carboxylic acid−pyridine heterosynthons. For example, Nangia group reported two parallel triple interpenetrated 63-hcb networks based on cocrystallization of 2:3 1,3,5-cyclohexanetricarboxylic acid (CTA) and 1,2-bis(4-pyridyl)ethane23 and 2:3:1 CTA, 4,4′-bipyridine, and water.24 They also obtained 4-fold inclined interpenetrated 63-hcb networks based on 1:1 CTA and water.24 However, the triangular trimeric heterosython I is very rare in hydrogen-bonded supramolecular cocrystals.25 Effect of the Tecton Length on the Interpenetration Degree. Complexes 1 and 2 are comprised of three-connected triangular trimeric heterosython I and two-connected H2sub or H2seb linker, so the three-connected 2D networks with 63-hcb topology but with different interpenetration degree were obtained. The structural analysis indicates that the length of the tecton has little effect on the formation of the 63-hcb network but can obviously fine-tune the degree of interpenetration of the 2D networks. To the best of our knowledge, interpenetration can be sensitively affected by interactions between the neighboring networks, steric-hindrance groups, chemical functionality, and van der Waals surface areas of the organic tections.26 Although several strategies have been used to control interpenetration of metal-containing networks,27 how to control interpenetration of hydrogen-bonded organic networks is a huge challenge. Surprisingly and fortunately, the elongation of dicarboxylic acid left the topologies of the 1224



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CONCLUSIONS In this study, we have investigated the formation of the cocrystals between tmpbz and dicarboxylic acids of variable carbon chain length. Both cocrystals could be obtained by both solid−solid grinding with minor amounts of appropriate solvent and crystallization from solutions. The results of single-crystal X-ray diffractions have allowed the identification of two organic hydrogen-bonded 63-hcb networks with tmpbz and linear linkers H2sub and H2seb. Complexes 1 and 2 exhibit 4-fold and 5-fold parallel interpenetration of 63-hcb networks, respectively, which depends on the length of the dicarboxylic acid. This work elucidates a rare example that interpenetrated hydrogenbonded networks could be ingeniously controlled by the length of linker, although this controllability has already been achieved in metal−organic coordination polymers. The photoluminescence investigation suggests that cocrystallization could be employed to modulate the emission of the single component. The application of this modulation strategy and mechanochemical synthesis protocol to other supramolecular cocrystal systems is currently under investigation.

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ASSOCIATED CONTENT

S Supporting Information *

Crystallographic data in CIF format and TGA for 1 and 2. This material is available free of charge via the Internet at http:// pubs.acs.org.

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AUTHOR INFORMATION

Corresponding Author

*E-mail: [email protected]. Funding Figure 3. Experimental powder diffraction patterns of 1 and 2 as obtained from solution and by grinding, compared with the theoretical powder pattern calculated on the basis of single crystal data.

This work was supported by the NSFC (Grant No. 21201110), the Special Funding of China Postdoctoral Science Foundation (Grant 2013T60663), and Research Award Fund for Outstanding Middle-aged and Young Scientist of Shandong Province (Grant BS2013CL010). Notes

The authors declare no competing financial interest.

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REFERENCES

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Figure 4. Photoluminescence of 1 and 2 at 298 and 77 K.

cocrystallized forms were changed.29 At lower temperature, the hydrogen bonding interactions as well as the rigidity of network were strengthened; hence enhanced emissions were observed. This interesting result demonstrated the possibility of photoluminescence modulation by way of cocrystallization. 1225



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Solution and Mechanochemical Syntheses of Two Novel Cocrystals

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