Article pubs.acs.org/crystal
Two Thermochromic Layered Iodoargentate Hybrids Directed by 4and 3‑Cyanopyridinium Cations Tanlai Yu, Li An, Lin Zhang, Junju Shen, Yangbo Fu, and Yunlong Fu* School of Chemistry & Material Science, Shanxi Normal University, Linfen 041004, P. R. China S Supporting Information *
ABSTRACT: Two layered iodoargentates, [HCP][Ag2I3] (HCP+ = NH-4-cyanopyridinium) (1) and [MCP][Ag4I5] (MCP+ = N-methyl-3-cyanopyridinium) (2) have been solvothermally synthesized. For 1, the inorganic layer is built up by 4-connected Ag4I8 unit with cubane-type Ag4I4 core via sharing peripheral μ2-I in ab plane, while the HCP+ cations are located at the apertures and interlayer space. For 2, the inorganic layer is constructed from [Ag6I6]n and [AgI3]n2n− chains via alternative corner- and edge-sharing modes along the b-axis, while the MCP+ cations lie between neighboring layers. Compounds 1 and 2 exhibit reducing band gaps relative to the bulk β-AgI and remarkable thermochromism, which are ascribed to the intermolecular charge transfer (CT) and affected by electron affinity of pyridinium cations.
1. INTRODUCTION Since the mid-1980s, fabrication of inorganic−organic hybrids has attracted much attention due to their distinctive properties inherited from inorganic and organic components in one material, as well as potential intriguing properties arising from their interactions.1−4 Especially, preparative and functional research of halometallate hybrids based on their flexible molecular engineering and energy band engineering represents a new trend in solid state chemistry,5−9 which have resulted in diverse structures and novel properties, such as switchable NLO devices,10,11 visible-light sensitizers for photovoltaic cells,12,13 and chromism.14−23 All of these largely depend on the nature of structural directing agents (SDAs). Although much effort has been paid to modulate the structures and properties of halometallate hybrids by various SDAs such as organic cations and metal complexes, properties arising from organic and inorganic interactions are rarely given much attention. Pyridinium cations have potential applications in solar energy storage, second-harmonic generation (SHG) materials, catalytic, agrochemical, surfactant, and optoelectronic materials.24−32 Especially, pyridinium halides can form charge transfer complexes and reveal diversiform chromism, such as photochromism, thermochromism, solvatochromism, and electrochromism, which mainly occurred in liquid crystals, as well as solution and film systems.33,34 Furthermore, although a large amount of thermochromic materials have been developed and found wide applications, low temperature reversible thermochromic materials are still rare.35,36 Recently, the introduction of viologen into chlorobismuthates and halozincates have led to some interesting photochromic materials and further structural elucidation of photochromism.20−22 Obviously, protonated and alkylated pyridinium cations possess various structures and © 2014 American Chemical Society
tunable electron affinities, and hybridization with hyperpolarizable halometallates will endow them with unique structural directing effects and energy band tuning ability.37−40 Herein, we report two layered iodoargentate hybrids, [HCP][Ag2I3] (1) and [MCP][Ag4I5] (2), which exhibit adjustable structural variations and interesting low-temperature reversible thermochromism.
2. EXPERIMENTAL SECTION 2.1. Materials and Methods. All reagents and solvents were commercially available and used as received without further purification. The Fourier-transform infrared spectroscopy (FT-IR) spectra were recorded from KBr pellets in the range of 4000−400 cm−1 on a Nicolet 5DX spectrometer. X-ray powder diffractions (XRPD) were measured on a Rigaku UItima IV-185 diffractometer. Elemental analyses were carried on PerkinElmer 240 elemental analyzer. Optical diffuse reflectance spectra were measured at room temperature and 77 K with a Varian Cary 5000 UV−vis spectrophotometer, and pure powder samples were used (the values of Eg were obtained with the use of a straightforward extrapolation method41,42). 4-Cyanopyridine (4-cypy) and 3-cyanopyridine (3-cypy) were chosen as SDAs and electron acceptors due to their distinct steric effects and electron affinity. 2.2. Preparation of [HCP][Ag2I3] (1). A mixture of AgI (0.704 g, 3.0 mmol), 4-cypy (0.068 g, 0.65 mmol), acetone (5.0 mL), and concentrated HI (0.35 mL, 45%) was stirred for 30 min at room temperature, then sealed in a 15 mL Teflon-lined stainless steel vessel, heated at 110 °C for 3 days, and cooled to room temperature. Red plate crystals were obtained in 32.5% yield (based on Ag). Anal. Calcd for C6H5N2Ag2I3: C 10.27, H 0.72, N 3.99%. Found: C 10.26, H 0.74, Received: March 31, 2014 Revised: July 11, 2014 Published: July 16, 2014 3875
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Table 1. Crystal Data and Structure Refinement for 1 and 2 at 293 and 100 K compound CCDC code temperature empirical formula formula weight crystal size (mm) crystal system space group a (Å) b (Å) c (Å) α (deg) β (deg) γ (deg) volume (Å3) Z Dc (g cm−3) F(000) μ (mm−1) reflections collected unique reflections Rint goodness-of-fit on F2 R1/wR2, [I ≥ 2σ(I)]a,b R1/wR2, (all data) Δρmax/Δρmin (e Å−3) a
1 993061 293(2) K C6H5N2Ag2I3 701.56 0.12 × 0.11 × 0.04 orthorhombic Cccm 10.4841(6) 12.8540(9) 20.8593(15) 90 90 90 2811.1(3) 8 3.315 2464 9.341 3600 1426 0.0613 1.139 0.0633, 0.1517 0.0794, 0.1620 1.186, −1.049
2 993062 100(2) K C6H5N2Ag2I3 701.56 0.13 × 0.11 × 0.05 orthorhombic Cccm 10.3473(7) 12.8314(9) 20.581(2) 90 90 90 2733.3(7) 8 3.411 2464 9.609 3342 1340 0.0809 1.257 0.1051, 0.1879 0.1094, 0.1900 3.008, −2.517
993063 293(2) K C7H7N2Ag4I5 1185.13 0.13 × 0.08 × 0.06 monoclinic P2(1)/n 12.5025(6) 8.0208(4) 19.6131(8) 90 99.407(4) 90 1940.35(16) 4 4.057 2064 11.918 7851 3813 0.0386 1.044 0.0597, 0.1580 0.0798, 0.1812 2.212, −2.380
993064 100(2) K C7H7N2Ag4I5 1185.13 0.13 × 0.08 × 0.06 monoclinic P2(1)/n 12.2470(3) 8.00163(15) 19.7579(5) 90 100.375(2) 90 1904.54(7) 4 4.133 2064 12.142 8250 3737 0.0211 1.058 0.0248, 0.0507 0.0308, 0.0529 0.907, −0.894
R1 = ∑∥F0| − |Fc∥/∑|F0|. bwR2 = [∑w(F02 − Fc2)2/∑w(F02)2]1/2.
Figure 1. (a) [Ag2I3]nn− layer of 1 constructed from Ag4I8 unit via corner-sharing modes. (b) Packing diagram of 1 showing the position of HCP+ cations. N 4.01%. IR (KBr, cm−1): 3111m, 2924w, 2845w, 2245w, 1633s, 1448m, 1399s, 1126w, 817w, 769w, 700w, 596w, 528w, 485w. 2.3. Preparation of [MCP][Ag4I5] (2). A mixture of AgI (0.704 g, 3.0 mmol), 3-cypy (0.104 g, 1.0 mmol), acetonitrile (5.0 mL), methanol (1.0 mL), and concentrated HI (0.18 mL, 45%) was stirred for 30 min at room temperature, then sealed in a 15 mL Teflon-lined stainless steel vessel, heated at 110 °C for 3 days, and cooled to room temperature. Yellow rod crystals were obtained in 53.4% yield (based on Ag). Anal. Calcd for C7H7N2Ag4I5: C 7.09, H 0.60, N 2.36%. Found: C 7.11, H 0.57, N 2.37%. IR (KBr, cm−1): 3063m, 2912w, 2853w, 2252w, 1631m, 1497m, 1460w, 1403w, 1293w, 1243w, 1138s, 916w, 807w, 664m, 616w, 548w. 2.4. X-ray Crystallography. Single-crystal X-ray diffraction data were collected at 293 and 100 K on an Oxford Gemini diffractometer (Mo Kα, λ = 0.71073 Å), respectively. An empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.43 The structures were solved by direct methods and refined on F2 by full-matrix least-squares methods with
the SHELXS-97 program.44 The HCP+ cations in 1 are disordered (Figure S1, Supporting Information). The crystallographic data of 1 and 2 are listed in Table 1, and the selected bond lengths and bond angles are listed in Table S1, Supporting Information.
3. RESULTS AND DISCUSSION 3.1. Structural Description. 3.1.1. [HCP][Ag2I3] (Red, 1). Complex 1 crystallizes in the orthorhombic space group Cccm and exhibits a 2D layered structure. The asymmetric unit of 1 contains one silver(I) atom, two iodine atoms, and disordered HCP+ cations. Each Ag atom is four-coordinated in a distorted tetrahedral geometry by three μ3-I atoms and one μ2-I atom. The Ag−I bond distances and the I−Ag−I bond angles are 2.7940(7)−2.9241(7) Å and 99.51(2)−119.22(2)°, respectively. As shown in Figure 1a, each inorganic layer [Ag2I3]nn− is composed of cubane-type Ag4I8 clusters by sharing four μ2-I 3876
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Figure 2. (a) [Ag4I5]nn− layer of 2 is constructed from [Ag6I6]n chain (A) and [AgI3]n2n− chain (B). (b) Packing diagram of 2 showing the position of MCP+ cations.
along the (1,1,0) and (1,1̅,0) direction respectively, in which the Ag···Ag distance is 3.3537(12) Å, implying the existence of argentophilic interactions. Noteworthy, the disordered HCP+ cations in polymeric structure have two kinds of configurations (Figure 1b). One is trapped within the cavity of [Ag2I3]nn− layer and perpendicular with inorganic layer, displaying a significantly structural directing effect; the other is positioned at interlayer space and parallel to inorganic layer. Although the Ag4I8 unit is not surprising in relation to the published structures {[N(C3H7)4]4(Ag4I8)} (0D),45 [(APHEN-H)2(Ag4I6)]n (1D),38 {(DABP)[Ag4I6]} (1D),46 and [(N-mepipzH2·2DMSO)(Ag 4I6 )]n (3D),47 the layered iodoargentate based on [Ag4I4]I4 unit is not reported so far, indicating the delicate flexibility of iodoargentate frameworks and unique structural directing effect of HCP+ cations. 3.1.2. [MCP][Ag4I5] (Yellow, 2). Complex 2 crystallizes in the monoclinic space group P2(1)/n and exhibits a different 2D layered structure, the asymmetric unit of 2 contains four silver(I) atoms, five iodine atoms, and one MCP+ cation. Each Ag(I) atom adopts a distorted tetrahedral coordination geometry. The Ag−I bond distances and the I−Ag−I bond angles are 2.7851(5)−3.0237(5) Å and 102.351(16)− 114.883(16)°, respectively. The Ag···Ag distances range from 3.1899(6)−3.2232(9) Å, implying the existence of argentophilic interactions. As shown in Figure 2a, the inorganic layer is composed of two kinds of chains, [Ag6I6]n chain (A) with antiprism-like hexanuclear units and corner-sharing tetrahedral [AgI3]n2n− chain (B), which are alternatively connected together via corner- and edge-sharing modes along the b-axis. Despite that many complexes including double six-membered (D6R, hexagonal prism) rings have been reported, such as neutral Cu3I3 chain,48 Ag6I6 layer,49 and zeolites,50,51 compound 2 is the first 2D anionic structure based on the Ag6I6 hexagon prism unit. MCP+ cations only lie between the inorganic layers (Figure 2b). Obviously, MCP+ cation also exhibits excellent structural tuning ability on iodoargentate framework. It is known that structural directing agents (SDAs) affect the self-assembly of iodometallate anion mainly via the charge density and steric effect.52−55 Some researches indicate the spatial size and charge density of alkyl group have an important effect on the final structure of iodometallates.53,54 In this work, although two layered anionic iodoargentates are electircally
balanced by the similar spatial size and charge density of organic cations, a striking difference of bonding features between 1 and 2 reveals an obvious dependence of iodoargentate frameworks on the symmetry of organic cations. With the decrease of symmetry of SDAs, the inorganic moiety of 2 is much more complicated than that of 1, which can also be found in our previous work.47 In all, the introduction of new organic SDAs can greatly enrich the structures of inorganic framework. 3.2. Optical Absorption Spectra and Thermochromism. The purity of compounds has been proved by XRPD (Figure S3, Supporting Information), in which the experimental pattern is in good agreement with the theoretical simulation. The UV−vis spectra for 1 and 2 at ambient temperature and 77 K show characteristic excitonic absorption (277, 485 nm for 1 and 268, 391 nm for 2; Figure 3). The absorption edges can be
Figure 3. UV−vis spectra for 1 and 2 at room temperature (RT) and 77 K.
estimated as 1.89 eV for 1 and 2.63 eV for 2 (Figure S4, Supporting Information), indicating a semiconductor nature and remarkable red shift relative to the bulk β-AgI (2.81 eV). It is well-known that there usually exist intermolecular CT between pyridinium and electron donors such as halides and some electronic rich organic components; consequently, the 3877
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energy bands of electronic rich iodoargentates. Rational choice of aromatic cations and metal halides can be an effective route to the development of new functional materials of halometallates.
remarkable red shift of excitonic absorption for 1 and 2 should be ascribed to the intermolecular CT from pyridinium cations to iodoargentates.39,40,56,57 Especially, the band gap of 1 is redshifted by 0.74 eV with contrast to 2, which is also in good agreement with the colors of two iodoargentate hybrids and may be due to the high electron affinity of 4-cypy in contrast to 3-cypy.56−58 Noteworthy, two compounds show interesting low temperature thermochromism. Compound 1 undergoes a color change from red (room temperature, 293 K) to yellow (liquid nitrogen, 77 K) and 2 changes from yellow (293 K) to white (77 K) (Figure 4), exhibiting remarkable correlations with pyridinium
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ASSOCIATED CONTENT
S Supporting Information *
Disordered HCP+ of 1 (Figure S1), infrared spectroscopy (Figure S2), X-ray powder diffraction (XRPD) patterns (Figure S3), optical absorption spectra of 1 and 2 at room temperature (Figure S4), and selected bond lengths (Å) and angles (deg) (Tables S1 and S2). This material is available free of charge via the Internet at http://pubs.acs.org.
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AUTHOR INFORMATION
Corresponding Author
*(Y. L. Fu) Fax/Tel: +86 (0) 357 2053716. E-mail:
[email protected]. Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS We thank the National Natural Science Foundation of China (no. 21171110), the Research Fund for the Doctoral Program of Higher Education of China (no. 20131404110001), and the Natural Scientific Foundation Committee of Shanxi Province (no. 2009011009-4).
Figure 4. Thermochromic behaviors of 1 and 2: digital photographs of crystals taken at temperatures of liquid nitrogen (77 K) and room temperature (293 K).
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cations. The change occurred rapidly right after the crystal was put into liquid nitrogen, and this was reversible. To the best knowledge, reported thermochromic halometallates mainly include iodobismuthates and iodoplumbates, which are attributed to thermal induced phase transitions of perovskite iodoplumbates by the Billing group59,60 and lattice contraction shifts of the band edge by Loye group.15,61 However, no thermochromic iodoargentate was reported up to date, which may be due to the nature of parent compound AgI. Meanwhile, pyridinium-based materials usually possess interesting diversiform chromism in liquid crystals, as well as solution and film systems, which is attributed to the association and dissociation of CT complexes.33,62,63 The contrastive analysis of the single crystal and XRPD data collected at 100 and 293 K for 1 and 2 reveal no obvious structural changes or association/dissociation of CT complexs (Tables S1 and S2 and Figure S3, Supporting Information). Furthermore, UV−vis adsorption spectra (Figure 3) at room temperature and 77 K show no obvious shift of absorption band, implying a different thermochromic mechanism. Meanwhile, the absorption intensity is uniformly decreased for β-AgI in the range of 380 and 700 nm, whereas it is decreased in remarkablly different manners for 1 and 2 in the corresponding ranges, implying the crucial role of intermolecular CT in the thermochromism. It is possible that future electronic structure calculations may help explain these experimental observations; however, according to the above discussion, thermochromism of 1 and 2 is more likely ascribed to the temperature effects directly on the population of intermolecular charge transfer rather than on structural variations.
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