Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two

Article Cite This: Cryst. Growth Des. XXXX, XXX, XXX−XXX

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Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two Complementary π‑Bowls Published as part of a Crystal Growth and Design virtual special issue on π−π Stacking in Crystal Engineering: Fundamentals and Applications Cristina Dubceac,† Yulia Sevryugina,‡ Igor V. Kuvychko,§ Olga V. Boltalina,*,§ Steven H. Strauss,*,§ and Marina A. Petrukhina*,† †

Department of Chemistry, University at Albany, State University of New York, Albany, New York 12222, United States University of Michigan Library, Ann Arbor, Michigan 48109, United States § Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, United States ‡

S Supporting Information *

ABSTRACT: Designed synthesis of a new crystalline donor−acceptor organic hybrid has been accomplished by using two bowl-shaped polycyclic aromatic hydrocarbons (PAHs) having complementary structures and properties, namely, C20H10 and C5-C20H5(CF3)5. The X-ray structural characterization of the product, [(C20H10)·(C20H5(CF3)5)]·C6H4Cl2, revealed the formation of aligned columnar stacks of alternating C20H10 and C20H5(CF3)5 molecules with centroid-to-centroid distances of 3.658(8) and 3.787(8) Å and a small bowl slip of 0.086(6) Å. The tight bowl packing is accompanied by notable molecular geometry adjustments of the individual PAHs. The bowl depth increased for corannulene (Δ = +0.019 Å) and decreased for sym-pentakis(trifluoromethyl)corannulene (Δ = −0.011 Å), facilitating enhancement of concave−convex interactions along the stacks. The parallel alignment of one-dimensional columns is supported by multiple intermolecular interactions involving C6H4Cl2 used as the crystallization solvent, forming an infinite twodimensional network in the solid state.

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INTRODUCTION Bowl-shaped polycyclic aromatic hydrocarbons (PAHs) with nonplanar carbon frameworks have attracted special attention as open substructures of fullerenes in recent years.1−5 Corannulene (C20H10, 1, Scheme 1), the smallest curved fragment of C60-fullerene, was first prepared in 1966 by a multistep low-yield synthesis.6,7 More practical routes based on flash vacuum pyrolysis8,9 and solution phase synthetic techniques10,11 were later developed, allowing broad investigation of corannulene properties and applications. Controlled

derivatization at the rim of 1 with various substituents significantly modulated the properties of the corannulene bowl.12−18 For example, rim alkylation resulted in a stepwise increase in the electron density at the bowl core as the number of methyl substituents increases.19 In contrast, controlled fluorination at the rim significantly enhanced electron-accepting properties,20−22 affording π-bowls that are stronger electrophiles than C60.23 These studies revealed the potential of functionalized corannulenes as novel materials for organic lightemitting diodes (OLEDs), organic photovoltaic cells (OPVs), and organic field−effect transistors (OFETs).24−27 However, further development of these applications requires a better understanding and control of the solid-state packing in hybrid systems that can be achieved by tailoring the intermolecular interactions of the bowl-shaped building units. The X-ray crystal structural characterization of C20H10 revealed that the solid-state packing is dominated by C− H···π interactions with no long-range one-dimensional (1D) stacking of corannulene bowls.28,29 However, the increase in curvature of PAHs has been shown in many cases to result in

Scheme 1. Corannulene (Left) and symPentakis(trifluoromethyl)corannulene (Right)

Received: September 5, 2017 Revised: November 7, 2017

© XXXX American Chemical Society

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DOI: 10.1021/acs.cgd.7b01258 Cryst. Growth Des. XXXX, XXX, XXX−XXX

Crystal Growth & Design

Article

aligned concave−convex stacking of π-bowls based on enhanced dipole−dipole interactions.30−33 These X-ray crystallographic studies of solid-state structures of bowl-shaped PAHs have instigated investigations of unique optical and conducting properties exhibited by the crystalline organic materials.34−37 In addition, the shape complementarity required for effective promotion of dispersive interactions and enhancement of intermolecular concave−convex interactions has recently attracted special attention in host/guest supramolecular chemistry.38 Bowl-shaped PAHs have been tested as potential hosts for C60 and C70 fullerenes, and several resulting intermolecular hybrids of π-bowls with carbon π-balls have been characterized by X-ray crystallography.39−42 Moreover, craftily prepared organic receptors containing properly oriented corannulene bowls connected by predesigned linkers were utilized for strong binding of C60 through complementary π−π interactions.43−45 Computational and spectroscopic techniques were used to investigate the interactions of tetrathiafulvalene (TTF) derivatives with fullerenes and several bowl-shaped PAHs (C30H12, C32H12, C38H14).46−48 In addition, complexes of 7,7,8,8-tetracyanoquinodimethane (TCNQ) with corannulene have been structurally characterized to reveal ordered columnar assemblies in the solid state.49,50 In contrast, no studies of mixing different bowl-shaped PAHs as an entry to novel hybrid materials with new properties and applications have been reported to date. Inspired by the wellknown solid-state structure of the benzene/hexafluorobenzene adduct,51−53 we selected two complementary bowl-shaped building units, C5v-C20H10 and C5-C20H5(CF3)5 (1 and 2, Scheme 1), for the designed synthesis of an intermolecular organic hybrid. In addition to a good shape match, 1 and 2 should provide enhanced intermolecular electrostatic interactions for the concave−convex bowl placement, thus enforcing the aligned tight bowl stacking in the resulting crystalline material.

Figure 1. Top and side views of C20H10 (left) and C20H5(CF3)5 (right).

Figure 2. Concave−convex π−π stacking of C20H10 and C20H5(CF3)5 bowls in 3.

exhibited no bowl slip with a perfectly staggered alignment of the sym-pentakis(trifluoromethyl)corannulene molecules along the 1D stacks. Notably, the centroid-to-centroid distances of 3.796(2) Å in 2 are longer than those in 3, illustrating enhanced intracolumn interactions in the hybrid product 3. In contrast to 2, the corannulene derivative bearing five rim-bound tert-butyl groups does not exhibit any aligned packing. The bulky substituents in sym-pentakis(tert-butyl)corannulene prevent any close π−π intermolecular interactions, thus thwarting columnar stacking in the solid-state structure.55 It is interesting to compare the stacking pattern in the title hybrid (3) with the packing observed in the solid-state structure of deuterobenzene/hexafluorobenzene,52 which has 1D columns of alternating C6D6 and C6F6 molecules held together by strong π−π interactions of 3.355(4) Å. However, the distance between the centroids of the planar six-membered rings (3.763(3) Å) is longer than that in 3 due to a noticeable molecule slip of 1.493(4) Å along the stack propagation (Figure S4 in Supporting Information). Cocrystallization of corannulene 1 with its penta-substituted derivative 2 has a noticeable effect on the molecular geometry of individual bowls. The bowl depth of C20H10 increased from 0.875(2) Å in pristine corannulene29 to 0.894(8) Å in the cocrystal (3). The opposite effect was observed for C20H5(CF3)5, which has a smaller bowl depth in the mixed product (0.778(8) Å) than in sym-pentakis(trifluoromethyl)corannulene (0.789(2) Å) crystallized on its own54 (Δ = −0.011 Å). Notably, the remarkable transformation of the corannulene core has been previously observed in organometallic hybrid architectures. The bowl depth of C20H10 decreased in the adduct with Hg3 (0.758(22) Å), in which the corannulene framework undergoes significant geometrical adjustments (Δ = −0.117 Å) to enhance interactions with the geometrically and symmetrically mismatched electrophilic trimercury unit.56,57 We now provide a new example illustrating

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RESULTS AND DISCUSSION The solution crystal growth technique for mixing two bowls, C20H10 (1) and C20H5(CF3)5 (2), at the molecular level has been used. Colorless needles of the title product were grown by slow evaporation of a 1,2-dichlorobenzene solution containing an approximately equimolar mixture of 1 and 2 over a period of 4 days. The good quality of these crystals has allowed their successful X-ray diffraction characterization. The X-ray crystallographic study confirmed the formation of the product with a 1:1 bowl-to-bowl composition and inclusion of the crystallization solvent, giving an overall formula [(C20H10)·(C20H5(CF3)5)]·C6H4Cl2 (3). The product crystallizes in the centrosymmetric monoclinic space group P21/c with Z = 4 (see Table S2 for more details). The asymmetric unit contains one corannulene and one sym-pentakis(trifluoromethyl)corannulene along with a 1,2-dichlorobenzene molecule, with all atoms in general positions (see Figure S2). In the solid-state structure of 3, the two selected PAHs (1 and 2, Figure 1) form aligned 1D columns of alternating bowls based on their concave−convex π−π interactions (Figure 2). The resulting bowl stacking can be related to the enhanced dipole−dipole interactions between the interacting molecules in 3. There are two different distances of 3.658(8) and 3.787(8) Å between the bowl centroids within the column. The alignment of bowls along the stack is eclipsed with a very small bowl slip of 0.086(6) Å. Columnar stacking was not observed in crystals of 128,29 but was seen in pristine 2,54 which B



Article

Table 1. Average Bond Lengths (Å) of Corannulene and sym-Pentakis(trifluoromethyl)corannulene in 1, 2, and 3 PAH

C−C (hub)

C−C (spoke)

C−C (rim)

C−C (flank)

bowl depth

C20H10 (1) C20H10 in 3 C20H5(CF3)5 (2) C20H5(CF3)5 in 3

1.4151(16) 1.411(8) 1.414(19) 1.409(8)

1.3790(14) 1.383(8) 1.371(2) 1.377(8)

1.3831(15) 1.377(8) 1.385(18) 1.394(8)

1.4464(16) 1.446(8) 1.451(19) 1.445(8)

0.875(2) 0.894(8) 0.789(2) 0.778(8)

the inherent flexibility of the carbon framework of corannulene: it is able to increase its curvature by Δ = +0.019 Å. Considering other geometric parameters, the hub, spoke, rim, and flank C−C bonds of C20H10 in 3 remain almost unchanged (Table 1). The C−C and C−CF3 bond lengths in C20H5(CF3)5 also exhibit very small alterations, with only a slight lengthening of the rim and spoke C−C bonds and a complementary shortening of the hub and flank bonds. The calculated p-orbital axis vector (POAV) pyramidalization angles58,59 are also in agreement with the increased curvature of corannulene core in 3. The hub and spoke POAV angles of C20H10 are increased, while the rim carbon atoms become planar with a 0° POAV angle (Table S1). On the other hand, the bowl of sym-pentakis(trifluoromethyl)corannulene suffers a decrease of its core POAV angles (hub, spoke, and rim) in 3 when compared to 2. The C atoms that are bound to or are part of the trifluoromethyl groups in 3 have a slightly enhanced deviation from planarity relative to 2. Both curved building units in 3 have POAV angles of 0° for the unfunctionalized carbon atoms, while the CF3-bearing rim carbon atoms in C20H5(CF3)5 have an average POAV angle of 0.539(5)°. In the solid-state structure of 3, the 1D columns alternate along the crystallographic c axis with adjacent stacks facing in opposite directions (Figure 3). This alignment is supported by different types of intermolecular interactions involving 1,2dichlorobenzene (1,2-DCB). Notably, our attempts to grow crystals from benzene failed, illustrating the important role of 1,2-DCB in the solid state packing of 3. Specifically, the C20H5(CF3)5 molecule interacts with the solvent through (C)H···F contacts as short as 2.659(7) Å and a C−H···F angle

of 115.36°, which fall in the range of previously reported values.60−62 There are also T-shaped C−H···π contacts of 2.733(8) Å originating on the rim C−H site of corannulene and perpendicular to the aromatic ring of 1,2-DCB. On the opposite side of the six-membered ring, the 1,2-DCB molecule interacts with a corannulene bowl from another column through a (C)H···Cl contact of 2.909(7) Å with a C−H···Cl angle of 133.40°. These parameters are similar to those found in the literature.63−65 The solvent molecules in 3 are oriented in a particular manner, with the two chlorine atoms of 1,2-DCB facing in the direction opposite to the 1D column’s orientation (Figures 4

Figure 4. View down the b axis in 3 showing the orientation of 1,2DCB molecules with respect to corannulene bowls.

and S3). The propagation of the hybrid columns differs in different directions. While along the c axis every 1D column has both neighboring stacks of opposite orientation (Figure 3), the alignment along the a axis features every column having one neighboring stack oriented in the same direction and one in the opposite direction (Figure S6). Notably, each stack in the cocrystal includes only one of the enantiomers of the C5symmetric and chiral sym-pentakis(trifluoromethyl)corannulene (Figure 5). Overall, all of the stacks pointing “up” contain only one enantiomer and all of the stacks pointing “down” contain only the other enantiomer.

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CONCLUSIONS In summary, cocrystallization of two complementary bowls, C20H5(CF3)5 and C20H10, resulted in the first example of an organic hybrid that exhibits an aligned alternating bowl-stacked packing in the solid state. The selected π-bowls have a good size match and show enhanced concave−convex π−π interactions that manifest themselves through short bowl-tobowl distances along the 1D columns. The resulting tight stacking results in geometry adjustments of individual bowlshaped molecules, illustrating the inherent flexibility of their carbon frameworks which facilitate enhanced intermolecular interactions. This work demonstrates the potential of using complementary bowl-shaped building units in controlling and engineering the solid-state packing of curved PAHs as an entry to tuning the properties of the resulting organic hybrids.

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EXPERIMENTAL SECTION

Materials and Methods. The syntheses of corannulene66,67 and sym-pentakis(trifluoromethyl)corannulene54 were performed according to the established procedures. Corannulene was doubly sublimed at 175 °C prior to use. Anhydrous 1,2-dichlorobenzene was purchased

Figure 3. Alignment of 1D columns in 3 along the c axis with intercolumnar interactions shown in black (C−H···F), blue (C− H···π), and red (C−H···Cl); capped-sticks (top) and space-filling (bottom) representations. C



Article

Table of crystal structure and refinement details, table of POAV angles, ORTEP drawings (PDF) Accession Codes

CCDC 1535304 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_ [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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AUTHOR INFORMATION

Corresponding Authors

*E-mail: [email protected] (M.A.P.). *E-mail: [email protected] (O.V.B.). *E-mail: [email protected] (S.H.S.). ORCID

Steven H. Strauss: 0000-0001-7636-2671 Marina A. Petrukhina: 0000-0003-0221-7900 Notes

The authors declare no competing financial interest.

Figure 5. Orientation of 1D columns in the solid-state structure of 3 (“D” stands for downward orientation, “U” stands for upward orientation).

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ACKNOWLEDGMENTS Financial support of this work from the National Science Foundation, CHE-1608623 (M.A.P.) and CHE-1362302 (O.V.B. and S.H.S.), is gratefully acknowledged.

from Sigma-Aldrich, dried over 4 Å molecular sieves, and degassed prior to use. All manipulations were carried out using Schlenk line and glovebox techniques under an atmosphere of argon. 1H NMR spectra were measured on a Bruker AC-400 spectrometer at 400 MHz and were referenced to the resonance of the residual C6HD5 in C6D6. Crystallization of [(C20H10)·(C20H5(CF3)5)]·C6H4Cl2 (3). To a mixture of corannulene (1.0 mg, 0.004 mmol) and sym-pentakis(trifluoromethyl)corannulene (2 mg, 0.0034 mmol), 0.5 mL of 1,2dichlorobenzene was added. The resulting colorless solution was filtered into an L-shaped ampule, which was then sealed under reduced pressure. Slow evaporation of the solvent initiated by slight warming of one end of the sealed container afforded colorless needle-shaped crystals of 3 in 4 days. X-ray Data Collection and Structure Refinement. The X-ray quality crystals were coated with paratone oil and mounted onto a MiTeGen MicroMount fiber. Complete and redundant data were collected on a single flash-cooled crystal (T = 100 K using an Oxford Cryostream LT device) with a Bruker X8 Prospector Ultra X-ray diffractometer system equipped with a three-circle goniometer, an APEX II CCD area detector mounted on D8-platform, and a Cu−IμS (λ = 1.54178 Å) microfocus X-ray source operated at 30 W. The frames were collected with a scan width of 0.5° in ω and an exposure time of 20 s/frame. The intensity data sets consisted of φ and ω scans at a crystal-to-detector distance of 4.00 cm. The APEX II68 and SAINT69 software packages were used for data collection and data integration. The data were corrected for absorption effects using the SADABS empirical method.70 The structure was solved and refined by the full matrix least-squares techniques based on F2 (SHELXL-2014/ 6).71,72 The asymmetric unit of 3 contains one corannulene molecule, one sym-pentakis(trifluoromethyl)corannulene molecule, and one 1,2dichlorobenzene. All non-hydrogen atoms were refined with anisotropic thermal parameters, while all H atoms were included at geometrically idealized positions using a riding model. Further crystallographic data and X-ray experimental conditions for 3 are listed in Table S2 (Supporting Information). The CCDC reference number 1535304 contains the supplementary crystallographic data for 3.

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ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.7b01258. D



Article

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Self-Assembly of Aligned Hybrid One-Dimensional Stacks from Two

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