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Host-Guest Conversion: Transformation of Diiodomethane within 1DEnsemble Supra-channels into Triiodide-Iodine Channel via Photo-reaction Haeri Lee, Seo Young Hwang, Malenahalli Halappa Naveen, Yoon-Bo Shim, and Ok-Sang Jung Cryst. Growth Des., Just Accepted Manuscript • DOI: 10.1021/acs.cgd.8b00167 • Publication Date (Web): 13 Mar 2018 Downloaded from http://pubs.acs.org on March 15, 2018

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Crystal Growth & Design

Host-Guest Conversion: Transformation of Diiodomethane within 1D-Ensemble Supra-channels into Triiodide-Iodine Channel via Photo-reaction Haeri Lee, Seo Young Hwang, Malenahalli H. Naveen, Yoon-Bo Shim, and Ok-Sang Jung* Department of Chemistry, Pusan National University, Busan 46241, Korea

Self-assembly of ZnBr2 with 2,7-bis(isonicotinoyloxy)naphthalene (L) yields one-dimensional (1D) zigzag chains of [ZnBr2L] composition. This 1D chain ensemble forms unique suprachannels of 4.0 × 4.2 Å2 size via weak C−H···π and π···π interactions. 350 nm ultravioletirradiation effects “Host-Guest Conversion”. The transformation of diiodomethane molecules within supra-channel structure of CHCl3·CH2I2@[ZnBr2L] into unprecedented triiodide-iodine channel skeleton, HL+@[I3·I2]−. Specifically, two clear, quasi-reversible redox peaks were observed at +0.33 and +0.70 V versus Ag/AgCl in the anodic scan and at +0.19 and +0.62 V in the cathodic scan in acetonitrile for HL+@[I3·I2]−.

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Construction of desirable supra-channels in arrays of simple frameworks via geometric principles entailing Lego-like linkages promises to provide task-specific functional porous materials.1−9 If simple molecular units can be advantageously arrayed, what would that molecular assembly’s expected specific properties be? Research on the formation of such molecularassembled materials is an interesting topic to those seeking to understand their functions.10−14 Indeed, various assembled-channel materials for reversible exchange of small molecules have already been considered.15−19 For example, flexible assembled-channel materials of specific size are useful for control of lining properties such as hydrophilicity, surface area, and chirality.20−22 Thus, they are essential to specific applications in the fields of adsorption, gas storage, molecular recognition, anion exchange, and organic catalysis.7,24−28 A particularly hot issue right now is the adsorption and recognition of halomethane molecules, some of which are both widespread and hazardous. Halomethanes are found both naturally in marine environments and artificially in refrigerants, solvents, propellants, and fumigants.29−32 Many halomethanes, including chlorofluorocarbons, have attracted wide attention owing to the fact that when exposed to ultraviolet (UV) light at high altitudes, they become active and damage the Earth's protective ozone layer.33,34 Additionally to recognition, the transformation of channel-nestled halomethane molecules via photo-energy irradiation is a fascinating chemical methodology for generation of new chemical species.35 Such photoreactions via the in situ crystalline state are much more meaningful in that their new products cannot be obtained by general methods. In this context, research on unprecedented “Host-Guest Conversion” of arrayed channels has been carried out. The assembled-channel materials of 1D coordination polymers, CHCl3·CH2I2@[ZnBr2L] (L = 2,7-bis(isonicotinoyloxy)naphthalene as a bent bidentate ligand) has been changed into an


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unprecedented triiodide-iodine, HL+@[I3·I2]−, channel in the crystalline state via in situ photoreaction. In the present study, a new bidentate ligand, 2,7-bis(isonicotinoyloxy)naphthalene (L), was prepared by reaction of 2,7-dihydroxynaphthalene with isonicotinoyl chloride hydrochloride according to the procedure available in the literature.36 L is soluble in common organic solvents such as chloroform, dichloromethane, and tetrahydrofuran, but insoluble in water, diethyl ether, and n-hexane. Self-assembly of ZnBr2 with L in EtOH/CHCl3/CH2I2 gives rise to onedimensional (1D) zigzag coordination polymers of CHCl3·CH2I2@[ZnBr2L], as depicted in Scheme 1. All of the present compounds were analyzed by X-ray crystallographic analysis (Table 1). Our results confirmed that product formation was not affected by the change of reactant mole ratio or concentration under the given conditions, indicating that the 1D zigzag skeletal structure was thermodynamically stable. The zigzag 1D coordination polymers form assembled-channels. Each Zn(II) center has a typical tetrahedral geometry with two pyridyl N-donors from two Ls and two bromides. The bent L, as an N-donor, connects two zinc(II) ions in a µ2-fashion, thus affording zigzag 1D coordination polymers with one turn of ZnL (Figure S1). Two halide anions bound to Zn(II) play a significant role in the formation of 1D pitches with N−Zn−N = 106.0(2)° and Br−Zn−Br = 122.85(5)°. The distance between Zn(II) and N ranges from 2.059(6) to 2.078(6) Å. The zigzag 1D skeletons form a molecular array (10 -1 direction) with suprachannels of 4.0 × 4.2 Å2 for [ZnBr2L], respectively. The molecular arrays are formed by the presence of weak C−H···π (2.68(1) Å) and π···π interactions (3.31(1) Å) (Figure S2). Another significant aspect of the molecular ensembles is the fact that the nestled solvate molecules have little tendency to serve as common ‘‘template effects,’’ for the formation of supramolecular 3 ACS Paragon Plus Environment


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ensemble in the solid state. Within those assembled-channels, the solvate molecules are nestled. The air-stable crystals are insoluble in common organic solvents but easily dissociated in dimethyl sulfoxide and N,N-dimethylformamide. The present thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) results for CHCl3·CH2I2@[ZnBr2L] showed drastic decomposition at 404 °C, corresponding to the collapse of the 1D skeletal structures (Figure S3). The relevant bond lengths and angles of all of the crystal structures are listed in Table 2, and the crystal structures and contact voids of CHCl3·CH2I2@[ZnBr2L] are depicted in Figure 1. The solvent-accessible volume, as calculated by PLATON,37 was estimated to be 529.7/1495.7 (35.4%) Å3 for CHCl3·CH2I2@[ZnBr2L]. The solvate molecules within the assembled-channels indicated that the channels are hydrophobic, which is to say, that they contained no alcohol or water molecules. However, an important feature is that each channel significantly adsorbs various halomethanes. The [ZnBr2L] crystalline solids could be filled with various solvate molecules in the order CH2Br2 > CH2Cl2 > CH2I2 > CHCl3 (Figure S4). The powder XRD pattern for the solvent-exchanged crystalline solid was consistent with that of the original crystal, as plotted in Figure S5. 350 nm UV irradiation of CHCl3·CH2I2@[ZnBr2L] crystals in mother liquor of EtOH/CHCl3/CH2I2 (v/v/v = 4 : 2 : 1) at room temperature resulted in the formation of unprecedented red crystalline solids consisting of HL+@[I3·I2]−, which very stable photoproducts cannot be synthesized by general methods. Under UV irradiation, CH2I2 molecules are known to decompose, producing several species such as CH2I−, :CH2, I2, and I−.38 CHCl3·CH2I2@[ZnBr2L] became to dissolve into the solvent system. L is protonated by HI3 or HI formed from photo-dissociation of diiodomethane molecules. Neat chloroform can be photodecomposed by the catalytic effect of several chlorometallate complexes under UV irradiation.39 4 ACS Paragon Plus Environment

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Even though the mechanism of catalysis is still debated, to the best of our knowledge, chloroform molecules are, in fact, photo-dissociated to form HCl and CCl3 radicals.40,41 Subsequently, Zn(II) ions are trapped by chloride, and successive reactions of H+ with pyridyl ligand give rise to quaternary ammonium salt-type HL+. Such a reaction condition under UV irradiation, in other words, stabilizes the crystals in chloroform media, which solubilized species then react with the dissociated H+, I3−, and I2. In our present case, the photoreaction — along with the concomitant formation of the triiodide-iodine channel via the in situ crystallization process — was complete within 8 h (Figure S6). Of course, the adsorbed CH2I2 within suprachannels plays an important role in photoreactions. The reactions proceeded irrespective of moisture, indicating that the proton source of the quaternary ammonium salt is not trace water. TGA and DSC results for HL+@[I3·I2]− showed drastic decomposition at 285 °C (Figure S7). 1H NMR spectrum of HL+@[I3·I2]− in MeCN-d3 and IR spectrum were designated in Figures S8−9. What is the critical driving force behind the efficient formation of such unique photo-products? We ascribed it to the in situ crystallization of the thermodynamically stable three-dimensional channel skeleton of HL+@[I3·I2]− (Figure S10). A unique 3D framework was formed via interactions of I−I···I−I−I = 3.30(1), 3.79(1) Å with channels (001; 5.4 × 7.9 Å2; 66(3)°, 114(2)°) and (100; 6.1 × 11.2 Å2; 60.5(3)°, 119.3(9)°). The crystal structure of HL+@[I3·I2]− is depicted in Figure 2. Note that the weak interactions are longer than the distances of I−I = 2.785(2), 2.7706(8) and I−I−I = 3.0909(6), 2.7914(6) Å. Of course, the bent degree (130.4(1)°) of HL+@[I3·I2]− was spread out relative to that (117.7(2)°) of [ZnCl2L]. The π···π interaction of [HL]+···[HL]+ was 3.27(1) Å. The Raman spectra of HL+@[I3·I2]− crystals showed that the very strong band at 108 cm−1 corresponds to the characteristic mode of the I3− species (Figure S11).42 The UV spectrum (Figure S12) of HL+@[I3·I2]− appeared at 262 (shoulder), 287, and 362 nm. In 5 ACS Paragon Plus Environment


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contrast, that of L showed λmax = 273 nm, and that of I2 appeared at 262, 290, 362, and 457 nm in MeCN. The cyclic voltammograms (CVs) recorded for HL+@[I3·I2]− and L are presented in Figure 3. For HL+@[I3·I2]−, two redox peaks were clearly observed at +0.33 and +0.70 V versus Ag/AgCl in the anodic scan and the corresponding peaks at +0.19 and +0.62 V in the cathodic scan in acetonitrile (Figure 3a). The mixture of L and HI in N,N-dimethylformamide showed two anodic peaks at +0.50 and +0.78 V and two small cathodic peaks at +0.08 and +0.60 V, respectively. However, neither oxidation nor reduction peaks were observed for L in dichloromethane. The redox peaks of HL+@[I3·I2]− were further confirmed by comparison with those of iodine in acetonitrile containing 0.1 M TBAP (Figure 3b). The two anodic peaks of HL+@[I3·I2]− are attributed to the oxidation of iodide ions to triiodide ions, and then triiodide to iodine, according to the equations43: 3I−

I3− + 2 e−

2I3−

3I2 + 2 e−

The ∆E values of the quasi-reversible redox peaks of HL+@[I3·I2]− were determined to be 150 and 90 mV, while those for iodine were 290 and 90 mV. The smaller difference in ∆E of HL+@[I3·I2]− than that in ∆E of I2 explains that HL+@[I3·I2]− is more reversible electron-transfer system than free iodine in solution. Such an efficient redox system is partly indebted to the cationic guest HL+ effect. In solution, the supramolecular structures were only partially conserved, as were the intermolecular interactions between HL+ and triiodide and between the HL+s. In conclusion, the 1D ensemble’s assembled-channels were demonstrated to efficiently absorb and desorb halomethane molecules without destruction of the skeleton. Furthermore, 6 ACS Paragon Plus Environment

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unprecedented “Host-Guest Conversion” transformations under UV irradiation via in situ crystallization in specific media were accomplished. Thus, this system can be considered to represent a landmark conceptual research achievement of a novel in situ crystallization reaction together with selective photo-decomposition, which, intriguingly, can be advantageous in formulating new, specific chemical species. Further experiments and pervasive applications are in progress, the results of which certainly will yield more detailed information.



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Table 1. Crystal Refinement Parameters for CHCl3·CH2I2@[ZnBr2L] and HL+@[I3·I2]−

CHCl3·CH2I2@[ZnBr2L] Formula Mw Cryst. sys. Space group a (Å) b (Å) c (Å) α (°) β (°) γ (°) V (Å3) Z ρ (g cm−3) µ (mm−1) Rint GoF on F2 R1 [I>2σ(I)]a wR2 (all data)b

C24H17N2O4Br2Cl3I2Zn 982.73 Triclinic P-1 11.0789(2) 11.2285(2) 12.5480(2) 102.8032(8) 94.4141(8) 98.5009(8) 1495.66(5) 2 2.182 5.858 0.0353 1.032 0.0592 0.1853

HL+@[I3·I2]− C22H16I5N2O4 1006.87 Monoclinic P21/c 13.5343(2) 10.7507(2) 19.4378(3) 106.841(1) 2706.96(8) 4 2.471 5.775 0.0405 1.035 0.0411 0.0784

a

R1 = Σ||Fo| – |Fc||/Σ|Fo|, bwR2 = [Σw(Fo2 – Fc2)2/ΣwFo2]1/2


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Table 2. Selected Bond Lengths (Å) and Angles (°) of CHCl3·CH2I2@[ZnBr2L] and HL+@[I3·I2]−

HL+@[I3·I2]−

CHCl3·CH2I2@[ZnBr2L] 2.059(6)

I(1)−I(1)#2

2.785(2)

2.078(6)

I(2)−I(2)#3

2.7706(8)

Zn(1)−Br(3)

2.349(1)

I(3)−I(4)

3.0909(6)

Zn(1)−Br(4)

2.361(1)

I(4)−I(5)

2.7914(6)

N(1)−Zn(1)−N(2)#1

106.0(2)

I(3)−I(4)−I(5)

174.63(2)

Zn(1)−N(1) Zn(1)−N(2)

#1

N(1)−Zn(1)−Br(1) #1

109.0(2)

N(2) −Zn(1)−Br(1)

106.6(2)

N(1)−Zn(1)−Br(2)

105.5(2)

#1

N(2) −Zn(1)−Br(2)

105.8(2)

Br(1)−Zn(1)−Br(2)

122.85(5)

Zn···Zn

18.6005(2)

#1

x,y+1,z−1 #2−x,−y+2,−z+1 #3−x+1,−y+1,−z



≡

+ ≡

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ZnBr2

≡ CH2I2

CHCl3·CH2I2@[ZnBr2L] hv in EtOH/CHCl3/CH2I2

Zn2+, Br−, :CH2, ·CCl3

HL+@[I3·I2]−

Scheme 1. Host-Guest Conversion Procedure for Supra-channel Structures


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(a)

a,c

b

(b)

Figure 1. (a) Packing structure and (b) contact voids of CHCl3·CH2I2@[ZnBr2L].



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(a)

a

b

(b)

b c

b

(c) c

Figure 2. (a) Top and (b) side views of HL+@[I3·I2]− (purple, I3−; pink, I2) and (c) hydrogen bonding (yellow dashed line) and π···π interaction (green) between quaternary ammonium salttype [HL]+.


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(a) 10

I/µA

0 -10 -20 0.0

0.4

0.8

1.2

E / V vs Ag/AgCl

(b) 10

I/µA

1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60


0 -10 -20 0.0

0.4

0.8

1.2

E / V vs Ag/AgCl

Figure 3. Cyclic voltammograms for (a) HL+@[I3·I2]− (black line), a mixture of L and HI (red line), and L (blue line), and (b) HL+@[I3·I2]− (black line) and I2 (red line) in acetonitrile containing 0.1 TBAP electrolyte, as obtained at a scan rate of 50 mV/s.



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ASSOCIATED CONTENT Supporting Information The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.cgd.xxxxxxx. Experimental details, crystal structures, intermolecular interactions, TGA and DSC curves, Powder X-ray diffraction patterns, 1H NMR, IR, Raman, UV-Vis spectra Accession Codes CCDC 1573789, 1573792 contain 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 [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

AUTHOR INFORMATION Corresponding Author *[email protected] Notes The authors declare no competing financial interest.

ACKNOWLEDGMENT 14 ACS Paragon Plus Environment

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This work was supported by the National Research Foundation of Korea (NRF) grant funded by the Korean Government [MEST] (2016R1A2B3009532 and 2016R1A5A1009405)

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For Table of Contents Use Only,

Host-Guest Conversion: Transformation of Diiodomethane within 1DEnsemble Supra-channels into Triiodide-Iodine Channel via Photo-reaction Haeri Lee, Seo Young Hwang, Malenahalli H. Naveen, Yoon-Bo Shim, and Ok-Sang Jung* Department of Chemistry, Pusan National University, Busan 46241, Korea

hv

Under UV irradiation, solvate diiodomethane molecules within 1D suprachannels have been transformed to triiodide-iodine channels through host-guest conversion. The photo-product is stable and quasi-reversible electron transfer system formed the composition of HL+, I3−, and I2.


HostâGuest Conversion: Transformation of ... - ACS Publications

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HostâGuest Conversion: Transformation of ... - ACS Publications