Crystal Engineering Based on Polymeric Hydrogen-Bonded

Crystal Growth & Design , 2005, 5 (3), pp 1041–1047. DOI: 10.1021/cg049650v. Publication Date (Web): February 25, 2005. Copyright © 2005 American ...
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CRYSTAL GROWTH & DESIGN

Crystal Engineering Based on Polymeric Hydrogen-Bonded Supramolecules by Self-Assembling of 4,4′-(9-Fluorenylidene)diphenol and 4,4′-Cyclohexylidenebisphenol with Bipyridines

2005 VOL. 5, NO. 3 1041-1047

Qingdao Zeng,* Dongxia Wu, Caiming Liu, Hongwei Ma, Jun Lu, Shandong Xu, Yan Li, Chen Wang,* and Chunli Bai* Center for Molecular Science, Institute of Chemistry, The Chinese Academy of Sciences, Beijing, 100080, People’s Republic of China Received October 14, 2004;

Revised Manuscript Received January 21, 2005

ABSTRACT: 4,4′-(9-Fluorenylidene)diphenol (FDP) and/or 4,4′-cyclohexylidenebisphenol (CBP) is crystallized with bipyridine bases 4,4′-bipyridyl (bipy), 1,2-bis(4-pyridyl)ethane (bipy-eta), 1,2-di(4-pyridyl)ethylene (dipy-ete), and 4,4′-dipyridyl N,N′-dioxide (dipy-dox) to afford molecular complexes (FDP)‚(bipy) 1, (FDP)‚(bipy-eta)0.5 2, (FDP)2‚ (dipy-ete) 3, (FDP)‚(dipy-dox) 4, and (CBP)‚(bipy) 5. The crystal structures of 1-5 have been determined by singlecrystal X-ray diffraction. All these molecular complexes exhibit polymeric supramolecular structures via O-H‚‚‚N or O-H‚‚‚O hydrogen-bonding. 1 forms double helices. 2 forms an infinite honeycomblike supramolecular structure. 3 forms a brick supramolecular structure. 4 forms an X-shaped supramolecular structure. 5 forms a single strand infinite helix. Thus, by changing the guest molecule, we can obtain different supramolecular hydrogen-bonded polymers through interactions of host-guest systems. Introduction

Chart 1

Crystal engineering and design of solid-state architecture are currently of great interest owing to their novel topologies and potential applications, such as in magnetism, catalysis, molecular recognition, ion exchange, small molecule inclusion, nonlinear optical behavior, electrical conductivity, molecular sensing, and, in general, the rational design of new materials.1-13 During the past few decades, a number of supramolecular architectures have been successfully designed and synthesized through self-assembly from different components by noncovalent, multiple intermolecular interaction.14-16 Recently, the most successful strategy for engineering the structures of crystals has been demonstrated using hydrogen-bonding interactions between molecules as the principal means to control molecular self-assembly during crystallization. This method takes advantage of the strong directionality of hydrogen bonds to organize individual molecules into supramolecular aggregates that have precise topological structures. These supramolecular aggregates often possess specific and useful chemical, physical, or optical properties due to the collective behavior of these weakly bound molecules. Particularly, intermolecular hydrogen-bonding interactions could provide precise topological control to design novel materials. The directional nature of hydrogen bonds is exploited in the organized self-assembly of molecules in solution and the solid state.17-19 The hydrogen-bonding between hydroxy and pyridyl is a useful and powerful organizing force and has been utilized for the formation of supramolecules.20 Both 4,4′-(9-fluorenylidene)diphenol (FDP) and 4,4′cyclohexylidenebisphenol (CBP) (Chart 1) are effective * To whom correspondence should be addressed. Tel: +86-1082614350. Fax: +86-10-82614350. E-mail: [email protected], [email protected], and [email protected].

10.1021/cg049650v CCC: $30.25 © 2005 American Chemical Society Published on Web 02/25/2005

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Table 1. Crystallographic Data for 1-5 cocrystal formula Mr crystal system space group T (K) a (Å) b (Å) c (Å) R (deg) β (deg) γ (deg) Z volume (Å3) Dcalc (g cm-3) µ (mm-1) 2θ scan range (deg) range h range k range l reflns collected unique reflns observed reflns goodness-of-fit R1, wR2 [I > 2σ(I)]

1

2

3

4

5

C35H26N2O2 506.58 monoclinic P2(1)/c 293(2) 12.511(3) 27.820(6) 23.127(5) 90 92.60(3) 90 12 8042(3) 1.255 0.078 2.30-54.72 -15 to 16 -34 to 35 -29 to 29 60638 17371 7869 0.969 0.0534, 0.1134

C31H24NO2 442.51 monoclinic P2(1)/n 293(2) 14.424(3) 10.901(2) 14.962(3) 90 95.24(3) 90 4 2342.7(8) 1.255 0.078 4.62-54.96 -18 to 18 -14 to 14 -19 to 19 17101 5289 1776 0.880 0.0536, 0.1201

C62H46N2O4 883.02 orthorhombic Pbca 293(2) 19.971(4) 10.782(2) 20.781(4) 90 90 90 4 4474.4(16) 1.314 0.082 3.92-44.98 0 to 21 0 to 11 -22 to 0 40161 2924 2118 1.022 0.0410,0.0899

C35H26N2O4 538.58 monoclinic C2/c 293(2) 18.988(4) 13.295(3) 11.009(2) 90 105.97(3) 90 4 2672.0(9) 1.339 0.088 3.78-54.96 -23 to 24 -16 to 17 -14 to 13 12801 3065 1952 1.030 0.0442, 0.1018

C28H28N2O2 424.52 triclinic P1 h 293(2) 6.2951(13) 7.6354(15) 25.366(5) 82.75(3) 87.55(3) 66.96(3) 2 1113.0(4) 1.267 0.080 3.24-54.96 -8 to 8 -8 to 9 -32 to 32 9335 4892 3228 1.051 0.0608, 0.1760

clathrate hosts in themselves.21 And both one FDP molecule and one CBP molecule molecule have two hydroxy groups, and one bipyridine molecule has two N or O atoms. Self-assembly via O-H‚‚‚N or O-H‚‚‚O hydrogen-bonding between FDP or CBP and bipyridines in EtOH was carried out. We anticipated that 1D supramolecular hydrogen-bonded polymer would be formed. With this in mind, we prepared five polymeric hydrogen-bonded supramolecules, (FDP)‚(bipy) 1, (FDP)‚ (bipy-eta)0.5 2, (FDP)2‚(dipy-ete) 3, (FDP)‚(dipy-dox) 4, and (CBP)‚(bipy) 5, by self-assembling of FDP or CBP with 4,4′-bipyridyl (bipy), 1,2-bis(4-pyridyl)ethane (bipyeta), 1,2-di(4-pyridyl)ethylene (dipy-ete), and 4,4′-dipyridyl N,N′-dioxide (dipy-dox), respectively. This paper describes our efforts to control molecular packing in crystalline materials by using hydrogen bonds as molecular building blocks. Experimental Section All materials (including FDP and CBP) were obtained from commercial suppliers (Acros Organics and Tokyo Kasei Kogyo Co., Ltd.) and were used without further purification. (FDP)‚(bipy) 1. An ethanolic solution of 4,4′-bipyridine (15.6 mg, 0.1 mmol) was slowly added to a 20 mL ethanolic solution of 4,4′-(9-fluorenylidene)diphenol (35.0 mg, 0.1 mmol) with stirring for 6 h at room temperature, and yellow crystals were obtained by slow evaporation of the solvent after a week. Anal. Calcd % (found %) for C35H26N2O2: C, 82.98 (82.61); H, 5.17 (5.27). (FDP)‚(bipy-eta)0.5 2. An ethanolic solution of 1,2-bis(4pyridyl)ethane (18.4 mg, 0.1 mmol) was slowly added to a 20 mL ethanolic solution of 4,4′-(9-fluorenylidene)diphenol (35.0 mg, 0.1 mmol) with stirring for 6 h at room temperature, and colorless crystals were obtained by slow evaporation of the solvent after a week. Anal. Calcd % (found %) for C31H24NO2: C, 84.14 (84.38); H, 5.47 (5.36). (FDP)2‚(dipy-ete) 3. An ethanolic solution of 1,2-di(4pyridyl)ethylene (18.2 mg, 0.1 mmol) was slowly added to a 20 mL ethanolic solution of 4,4′-(9-fluorenylidene)diphenol (35.0 mg, 0.1 mmol) with stirring for 6 h at room temperature, and light yellow crystals were obtained by slow evaporation of the solvent after a week. Anal. Calcd % (found %) for C62H46N2O4: C, 84.33 (84.16); H, 5.25 (5.16).

Table 2. Hydrogen Bond Metrics cocrystal 1

2 3 4 5

D-H‚‚‚A O(1)-H‚‚‚N(5) O(2)-H‚‚‚N(6)#1 O(3)-H‚‚‚N(3) O(4)-H‚‚‚N(2)#2 O(5)-H‚‚‚N(1) O(6)-H‚‚‚N(4) O(1)-H‚‚‚N(1) O(2)-H‚‚‚O(1) #2 O(1)-H‚‚‚N(1) #2 O(2)-H‚‚‚O(1)#3 O(1)-H‚‚‚O(2) O(1)-H‚‚‚N(1) #3

d(D-H)/ d(H‚‚‚A)/ Å Å 0.846(14) 0.819(14) 0.878(14) 0.814(14) 0.816(14) 0.847(14) 1.01(3) 0.89(3) 1.06(3) 0.90(2) 0.82(2) 0.82(3)

1.941(15) 1.969(15) 1.912(15) 1.946(16) 1.935(15) 1.948(15) 1.58(3) 1.84(3) 1.56(3) 1.81(2) 1.83(3) 1.96(3)

d(D‚‚‚A)/ Å

∠(DHA)/ deg

2.762(3) 2.774(3) 2.777(3) 2.740(3) 2.734(3) 2.789(3) 2.574(3) 2.687(3) 2.5910(19) 2.7040(18) 2.6515(19) 2.767(3)

163(2) 167(2) 168(2) 165(2) 166(2) 172(2) 166(3) 159(3) 163(2) 173(2) 175.6(3) 168.8(2)

(FDP)‚(dipy-dox) 4. An ethanolic solution of 4,4′-dipyridyl N,N′-dioxide dihydrate (22.4 mg, 0.1 mmol) was slowly added to a 20 mL ethanolic solution of 4,4′-(9-fluorenylidene)diphenol (35.0 mg, 0.1 mmol) with stirring for 6 h at room temperature, and brown crystals were obtained by slow evaporation of the solvent after a week. Anal. Calcd % (found %) for C35H26N2O4: C, 78.05 (78.16); H, 4.87 (4.69). (CBP)‚(bipy) 5. An ethanolic solution of 4,4′-bipyridine (15.6 mg, 0.1 mmol) was slowly added to a 20 mL ethanolic solution of 4,4′-cyclohexylidenebisphenol (26.8 mg, 0.1 mmol) with stirring for 6 h at room temperature, and colorless crystals were obtained by slow evaporation of the solvent after a week. Anal. Calcd % (found %) for C28H28N2O2: C, 79.22 (79.31); H, 6.65 (6.72). X-ray Data Collection, Structure Determination, and Refinement. The diffraction data for 1-5 were collected on a Rigaku RAXISRAPID automated diffractometer at room temperature using graphite-monochromated Mo KR radiation (R ) 0.71073 Å). The structure was solved by direct methods and successive difference maps (SHELXS 97)22 and refined by full-matrix least squares on F2 using all uniqe data (SHELXL 97).23 The non-hydrogen atoms were refined anisotropically. Crystal data and experimental details for the crystals of 1-5 are given in Table 1. Hydrogen bond metrics are given in Table 2.

Results and Discussion Synthesis. 4,4′-(9-Fluorenylidene)diphenol (0.1 mmol) or 4,4′-cyclohexylidenebisphenol (0.1 mmol) can be reacted with bipyridine (0.1 mmol) in an ethanol solu-

Polymeric Hydrogen-Bonded Supramolecules

Figure 1. (a) The crystal structure of 1. Hydrogen atoms were omitted for clarity. (b) The crystal-packing of 1 viewed down the a axis. Notice that 1 leads to 2D double helices. In the 1D helix, the angles and neighboring distances are ca. 112° and 9.36 Å, respectively. (c) Schematic representation of 1.

tion at room temperature. Crystals were obtained by slow evaporation of the solvent after a week. The product is (FDP)‚(bipy) 1, (FDP)‚(bipy-eta)0.5 2, (FDP)2‚ (dipy-ete) 3, (FDP)‚(dipy-dox) 4, and (CBP)‚(bipy) 5, respectively. Crystal Structure of (FDP)‚(bipy) 1. Single crystals of 1 (Figure 1) were obtained from ethanol solution after slow evaporation of the solvent at ambient conditions and examined using single-crystal X-ray diffraction methods. 1 gave a monoclinic crystal lattice with a P2(1)/c space group. All bond distances and angles of the molecule are normal. Selected crystal data and

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structural refinement parameters of 1 are given in Table 1, and hydrogen bond metrics are given in Table 2. The crystal structure of 1 is shown in Figure 1a. The asymmetric unit of 1 is composed of one molecule of each component connected by a FDP/bipy heterodimer. One FDP molecule is alternatively linked with two bipy molecules through two intermolecular O-H‚‚‚N hydrogen-bondings, thus stacking in an alternating pattern of ABABAB. Figure 1b shows the crystal packing of 1 down the a axis. The two H atoms in the OH group of FDP bond to two N atoms of two bipy molecules to form two intermolecular O-H‚‚‚N hydrogenbondings [O-H‚‚‚N: 0.846(14) Å, 1.941(15) Å, 2.762(3) Å, 163(2)°; 0.819(14) Å, 1.969(15) Å, 2.774(3) Å, 167(2)°; 0.878(14) Å, 1.912(15) Å, 2.777(3) Å, 168(2)°; 0.814(14) Å, 1.946(16) Å, 2.740(3) Å, 165(2)°; 0.816(14) Å, 1.935(15) Å, 2.734(3) Å, 166(2)°; 0.847(14) Å, 1.948(15) Å, 2.789(3) Å, 172(2)°]. The H‚‚‚N and O‚‚‚N bond lengths range between 1.912 and 1.969 Å and 2.734 and 2.789 Å with average lengths of 1.942 and 2.763 Å, respectively. The O-H‚‚‚N bond angles range between 163 and 172° with an average angle of 167°. The FDP molecule reverses alternatively in the polymeric hydrogen-bonded chain. This arrangement leads to a 1D infinite helix, with an angle of ca. 112°. These helices are parallel to each other, and their neighboring distances are 9.36 Å. In addition, two neighboring FDP molecules are packed head-to-tail; thus two neighboring helices are cross-linked to form the 2D double helices. The conformation and the relative orientation of double helices may be better understood from the schematic diagrams illustrated in Figure 1c. Crystal Structure of (FDP)‚(bipy-eta)0.5 2. Single crystals of 2 (Figure 2) were obtained from ethanol solution after slow evaporation of the solvent at ambient conditions and examined using single-crystal X-ray diffraction methods. 2 gave a monoclinic crystal lattice with a P2(1)/n space group. All bond distances and angles of the molecule are normal. Selected crystal data and structural refinement parameters of 2 are given in Table 1, and hydrogen bond metrics are given in Table 2. Figure 2a shows the crystal structure of 2. The asymmetric unit of 2 consists of two molecules of FDP and two equivalent halves of bipy-eta formimg two different FDP/bipy-eta heterodimers. Two FDP molecules are bridged by bipy-eta through two intermolecular O-H‚‚‚N hydrogen-bondings. Figure 2b shows the crystal packing of 2 down the b axis. One H atom in the OH group of one FDP molecule bonds to a N atom of the bipy-eta molecule to form an intermolecular O-H‚‚‚N hydrogen-bonding [O-H‚‚‚N: 1.01(3) Å, 1.58(3) Å, 2.574(3) Å, 166(3)°], and the O atom in the OH group bonds to the H atom in the OH group of another neighboring FDP molecule to form intermolecular O-H‚‚‚O hydrogen-bonding [O-H‚‚‚O: 0.89(3) Å, 1.84(3) Å, 2.687(3) Å, 159(3)°], thus forming an infinite honeycomb structure, in which there are four FDP and two bipy-eta molecules. The conformation and the relative orientation of the honeycomb repeating units in the 1D supramolecular polymeric structure are illustrated in Figure 2c. Crystal Structure of (FDP)2‚(dipy-ete) 3. Single crystals of 3 (Figure 3) were obtained from ethanol

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Figure 3. (a) The crystal structure of 3. (b) The crystalpacking of 3 viewed down the b axis. (c) Schematic representation of 3.

Figure 2. (a) The crystal structure of 2. Hydrogen atoms were omitted for clarity. (b) The crystal-packing of 2 viewed down the b axis. (c) Schematic representation of 2.

solution after slow evaporation of the solvent at ambient conditions and examined using single-crystal X-ray diffraction methods. 3 is associated with an orthorhombic crystal lattice with a Pbca space group. All bond distances and angles of the molecule are normal. Selected crystal data and structural refinement parameters of 3 are given in Table 1, and hydrogen bond metrics are given in Table 2. Figure 3a shows the crystal structure of 3. The asymmetric unit of 3 is composed of two molecules of

FDP and two halves of dipy-ete formimg two different FDP/dipy-ete heterodimers. One FDP molecule is alternatively linked with two dipy-ete molecules through two intermolecular O-H‚‚‚N hydrogen-bondings. Figure 3b shows the crystal packing of 3 down the b axis. Two FDP molecules are alternatively linked with two dipyete molecules through four intermolecular O-H‚‚‚N hydrogen-bondings [O-H‚‚‚N: 1.06(3) Å, 1.56(3) Å, 2.5910(19) Å, 163(2)°], thus forming a macrocycle. The oxygen atom in the OH group of all FDP molecules bonds to the hydrogen atom in the OH group of another neighboring FDP molecule to form intermolecular O-H‚‚‚O hydrogen-bonding [O-H‚‚‚O: 0.90(2) Å, 1.81(2) Å, 2.7040(18) Å, 173(2)°], thus forming a supramolecular brick structure. The conformation and the relative orientation of the brick repeating units in the 1D supramolecular polymeric structure have been depicted by schematic diagrams in Figure 3c. (FDP)‚(dipy-dox) 4. Single crystals of 4 (Figure 4) were obtained from ethanol solution after slow evaporation of the solvent at ambient conditions and examined using single-crystal X-ray diffraction methods. A monoclinic crystal lattice with a C2/c space group is identified. All bond distances and angles of the molecule are

Polymeric Hydrogen-Bonded Supramolecules

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Figure 4. (a) The crystal structure of 4. (b) The crystalpacking of 4 viewed down the c axis. (c) Schematic representation of 4.

normal. Selected crystal data and structural refinement parameters of 4 are given in Table 1, and hydrogen bond metrics are given in Table 2. Figure 4a shows the crystal structure of 4. The asymmetric unit of 4 consists of one molecule of each component connected by a FDP/dipy-dox heterodimer. One FDP molecule is alternatively linked with two dipydox molecules through two intermolecular O-H‚‚‚O hydrogen-bondings, thus stacking in an alternating pattern of ABABAB. Figure 4b shows the crystal packing of 4 down the c axis. The two hydrogen atoms in the OH group of FDP bond to two O atoms of two dipydox molecules to form two intermolecular O-H‚‚‚O hydrogen-bondings [O-H‚‚‚O: 0.82(2) Å, 1.83(3) Å, 2.6515(19) Å, 175.6(3)°]. The FDP molecule reverses alternatively in the polymeric hydrogen-bonded chain and two neighboring FDP molecules are packed headto-tail, resulting in an X-shaped supramolecular structure where there are two FDP and four dipy-dox molecules. The conformation and the relative orientation of the X-shaped repeating units in the 1D supramo-

Figure 5. (a) The crystal structure of 5. (b) The crystalpacking of 5 viewed down the a axis. Notice that 5 leads to the 1D infinite helix, whose angles and neighboring distances are ca. 107° and 7.56 Å, respectively. (c) Schematic representation of 5.

lecular polymeric structure have been depicted by schematic diagrams in Figure 4c. (CBP)‚(bipy) 5. Single crystals of 5 (Figure 5) were obtained from ethanol solution after slow evaporation of the solvent at ambient conditions and examined using single-crystal X-ray diffraction methods. 5 is identified as a triclinic crystal lattice with a P-1 space group. All bond distances and angles of the molecule are normal. Selected crystal data and structural refinement parameters of 5 are given in Table 1, and hydrogen bond metrics are given in Table 2.

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The crystal structure of 5 is similar to that of 1. Figure 5a shows the crystal structure of 5. The asymmetric unit of 5 contains one molecule of each component connected by a CBP/bipy heterodimer. One CBP molecule is alternatively linked with two bipy molecules through two intermolecular O-H‚‚‚N hydrogen-bondings, thus also stacking in an alternating pattern of ABABAB. Figure 5b shows the crystal packing of 5 down the a axis. The two H atoms in the OH groups of CBP bond to two N atoms of two bipy molecules to form two intermolecular O-H‚‚‚N hydrogen-bondings [O-H‚‚‚N: 0.82(3) Å, 1.96(3) Å, 2.767(3) Å, 168.8(2)°]. The CBP molecule reverses alternatively in the polymeric hydrogen-bonded chain. This arrangement leads to a onedimensional infinite helix, with an angle of ca. 107°. These helices are parallel to each other, and their neighboring distances are 7.56 Å. The conformation and the relative orientation of the helices may be better understood from the schematic diagrams illustrated in Figure 5c. The results of the X-ray structural studies involving host compound FDP in 1-4 showed two common features. One is related to the conformation sustained by FDP in all four structures where the planes of the fluorene backbone and the two phenolic units are twisted nearly perpendicular to each other (Figures 1-4). On the other hand, in the packings, the neighboring fluorene moieties have a parallel orientation, suggesting π-stacking interactions between these groups (Figures 1-4).21a In 5, the cyclohexane moiety of host compound CBP is in an almost perfect chair conformation,21c and the two phenolic units are twisted nearly perpendicular to each other (Figure 5). The conformations of the bipyridines play a crucial role in the design and construction of desirable frameworks. Among all bipyridine bases, because the length of bipy is the shortest and its rigidity is the strongest, both 1 and 5 form the helical structure, whereas bipy-eta and dipy-ete are longer and more flexible than bipy, and thus it is unfavorable for 2 and 3 to form the helical structure, but rather they form an infinite honeycomb structure and an infinite brick structure, respectively. The conformation of dipy-dox is somewhat different from those of the other three guest molecules; therefore 4 forms the X-shaped supramolecular structure. Conclusions In this work, 4,4′-(9-fluorenylidene)diphenol (FDP) and 4,4′-cyclohexylidenebisphenol (CBP) are used to construct supramolecular architectures based on crystal engineering. Throughout this study, it is observed that similar or different supramolecular hydrogen-bonded polymers would be formed through self-assembly via O-H‚‚‚N or O-H‚‚‚O hydrogen-bonding between FDP or CBP and bipyridines. The conformations of the bipyridines play an important role in the design and construction of desirable frameworks. The change of flexibility, length, and symmetry of the bipyridines could result in a class of materials containing diverse architectures and functions. Such studies are important to crystal engineering. It is possible to obtain novel topologies and extend the study to combinatorial libraries of intermolecular interactions for the exploration of forma-

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tion of various types of host-guest systems, by changing the guest molecule. Some related experiments are in progress. Acknowledgment. The authors thank the National Natural Science Foundation (No. 20103008) and the Foundation of the Chinese Academy of Sciences for financial support. Supporting Information Available: X-ray crystallographic data in CIF format. This material is available free of charge via the Internet at http://pubs.acs.org.

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