Conjugated Porous Networks Based on Cyclotriveratrylene Building Block for Hydrogen Adsorption

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* E-mail: [email protected] (Qiyu Zheng), [email protected] (Junmin Liu) Received March 31, 2013; accepted April 22, 2013; published online May 14, 2013. Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201300276 or from the author. Chin. J. Chem. 2013, 31, 617—623 © 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 617

DOI: 10.1002/cjoc.201300276

Conjugated Porous Networks Based on Cyclotriveratrylene Building Block for Hydrogen Adsorption

Xiaona Han,a Lei Li,b Zhitang Huang,a Junmin Liu,*,b and Qiyu Zheng*,a a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function,

Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China b School of Chemistry and Chemical Engineering, Institute of Physical Chemistry, Sun Yat-Sen University,

Guangzhou, Guangdong 510275, China

Macrocyclic CTV-Br3 reacted with the linear benzene-1,4-diboronic acid and 1,4-diethynylbenzene via Suzuki and Sonogashira-Hagihara coupling reactions producing the rigid porous materials CTV-CMP-1 and CTV-CMP-2. The porous materials have good thermal and chemical stability. The Brunauer-Emmet-Teller specific surface areas of CTV-CMP-1 and CTV-CMP-2 are 314 and 218 cm2•g−1, respectively. Physical properties of the porous materi-als were investigated, CTV-CMP-1 showed moderate hydrogen adsorption about 0.81 wt% at 1.13 bar while CTV-CMP-2 showed lower hydrogen adsorption about 0.51 wt%. These materials are analogs to activated carbons which could be potentially used in gas separation and organic compound adsorption.

Keywords cyclotriveratrylene, coupling reactions, conjugated microporous polymers, hydrogen adsorption

Introduction Due to the potential applications of microporous

materials in the field of gas storage, separation, and ca-talysis,[1] a broader variety of organic or organic/inorg-anic hybrid structures with either crystalline micropores or amorphous micropores have been produced in at-tempt to simulate traditional inorganic porous materials: zeolites and activated carbons. Metal-organic frame-works (MOFs)[2] and covalent-organic frameworks (COFs)[3] are crystalline porous materials. MOFs usu-ally have large pore sizes and surface areas but the frameworks are fragile to break down once the solvents are lost during reactions. This chemical instability prop-erty deteriorates their further utility. COFs are prepared by dynamic covalent controlled reactions with “error checking” and “proof-reading” characteristics like crys-tallization of small molecules. But there are limited re-actions to construct the dynamic covalent frameworks. And most reported COFs are also chem-sensitive. On the other hand, many reactions may be applied to pre-pare the amorphous microporous materials such as polymers of intrinsic microporosity (PIMs),[4] hy-per-cross-linked polymers (HCPs),[5] and conjugated microporous polymers (CMPs).[6] But due to the irre-versible process, polymers with high porousity and long-range order are hardly obtained. In spite of this, these materials have unique advantages, e.g., it is very convenient to incorporate multiple functional groups

into the organic microporous frameworks; most organic polymers are stable to harsh chemical conditions; and they have low skeleton density.

CMPs are widely investigated among the amorphous microporous materials for their optoelectronic proper-ties which could be applied to organic devices. They can be obtained via different reaction routes employing C－C coupling reactions such as Sonogashira-Hagihara coupling, Suzuki coupling reactions for theoretical in-vestigation as well as practical applications. Cooper[6c,7] reported the rigid microporous poly(aryleneethynylene) (PAE) networks and microporous poly(tri(4-ethynyl-phenyl)amine) networks which were synthesized through Sonogashira-Hagihara reaction. They found that the physical properties of these microporous networks could be controlled in a “quantized” fashion by varying the monomer structure length which is always demon-strated for order crystal materials. Their finding sug-gested that order is not a prerequisite for fine control over the microporous properties of organic networks. Chang[8] reported a serial of clickable, microporous, hydrocarbon particles synthesized through Sonogashira- Hagihara reaction. The post modification via Click re-action tailored the chemical and physical property of the microporous materials. In this way, the microporous materials could be derived to meet the specific applica-tion requirement. Jiang[9] reported a porous catalytic framework (FeP-CMP) which was synthesized via a Suzuki polycondensation reaction. FeP-CMP acted as a

Han et al.FULL PAPER

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heterogeneous catalyst for the activation of molecular oxygen to convert sulfide to sulfoxide and epoxidation of trans-stilbene. These built-in catalysts showed excel-lent reactivity because of the inherent open nanome-ter-scale pores that are accessible for substrates as well as the large surface areas (1270 m2•g−1).

Building units are crucial in exploring the porosity, porous structure, and gas adsorption capacities in mi-croporous materials. Recently, novel building blocks have been investigated for the construction of 3D CMPs in gas storage and organic molecules adsorption.[10] As the derivative of the cyclotriveratrylene (CTV), cyclotri-catechylene (CTC) has been incorporated in the micro-porous networks of PIM and COF as 3D building block.[11] Recently, we have also prepared the rigid CTV-based porous organic polymers through Click re-action.[12] These materials showed moderate to good hydrogen adsorption properties. More importantly, the rigid hydrophobic cavity of CTV could be as the second functional accommodation site compared to other building unit. Because of the convenient synthesis of CTV-Br3,[13] it seems that CTV could be an ideal 3D building block for construction of rigid CMPs.

Herein, we reported the targeted synthesis of CTV- CMP-1 and CTV-CMP-2 via Sonogashira-Hagihara coupling and Suzuki coupling reactions. For each mi-croporous material, the structure was confirmed by ele-mental analysis, IR spectroscopy, 13C NMR spectros-copy, TG analysis, and SEM; also the nitrogen and hy-drogen adsorption properties are investigated.

Experimental All chemical reagents were commercially available

and used as received unless otherwise indicated. CTV- Br3 was prepared by the reported method.[13]

Synthesis of CTV-CMP-1 and CTV-CMP-2 The synthesis of CTV-CMP-1 and CTV-CMP-2 is

shown in Scheme 1. For CTV-CMP-1, 250 mg (0.42 mmol) of CTV-Br3 and 1.7 equiv. of benzene-1,4- diboronic acid (BDBA) (120 mg, 0.72 mmol) were added to DMF (100 mL). The mixture was degassed by the freeze-pump-thaw cycles. To the mixture were added an aqueous solution of potassium carbonate (2.0 mol/L, 16 mL) and tetrakis(triphenylphosphine)palla-dium(0) (40.0 mg, 44 μmol). The resulting solution was degassed and purged with argon, and stirred at 150 ℃ for 36 h. After the mixture was cooled to room tem-perature, the insoluble precipitate was filtered and washed with water, aqueous hydrochloric acid, water, methanol, acetone, THF, dichloromethane, and pentane to remove any unreacted monomers or catalyst residues. After drying in vacuo an off-white powder was obtained (170 mg, 87%).

For CTV-CMP-2, 250 mg (0.42 mmol) of CTV-Br3 and 1.5 equiv. of 1,4-diethynylbenzene (80 mg, 0.64 mmol) were dissolved in the mixture of DMF (25 mL)

and triethylamine (25 mL) and the mixture was de-gassed by the freeze-pump-thaw cycles. To the mixture were added tetrakis(triphenylphosphine)palladium(0) (60 mg, 66 μmol) and copper(I) iodide (20 mg, 104.7 μmol). The resulting mixture was heated to 90 ℃ and stirred for 72 h under argon atmosphere. After the mix-ture was cooled to room temperature, the insoluble pre-cipitate was filtered and washed with water, aqueous hydrochloric acid, water, methanol, acetone, THF, di-chloromethane, and pentane to remove any unreacted monomers or catalyst residues. After drying in vacuo a yellow powder was obtained (205 mg, 89%).

Physical measurements TG analysis was performed using a TG/DTA6300

thermal analyzer at the heating rate of 10 ℃•min−1 in the N2 atmosphere. FT-IR spectra (film) were measured using a Nicolet 6700 Fourier transform infrared spec-trometer. Elemental analyses were carried out on Flash EA 1112. SEM analysis was performed on a JEOSJSM 6701F system. Solid-state cross polarization magic an-gle spinning (CP/MAS) NMR spectra were recorded on a Bruker Anence III 400 NMR spectrometer. Nitrogen adsorption isotherms were obtained on Quantachrome autosorb IQ2.

Results and Discussion As shown in Scheme 1, CTV-CMP-1 and CTV-

CMP-2 were synthesized via Suzuki and Sonogashira- Hagihara coupling reactions in DMF, which gave 87% off-white powder and 89% yellow powder, respectively. In order to make a full understanding of the bonding and structural features of polymeric network, FT-IR, 13C CP/MAS NMR, elemental analysis, nitrogen and hy-drogen adsorptions, and scanning electron microscopy analysis were carried out.

Figure 1 FT-IR spectra of CTV-Br3, CTV-CMP-1 and CTV-CMP-2.

FT-IR spectra gave useful information about the po-rous materials (Figure 1). A trace amount of water in KBr has been detected from the broad peaks at 3400 and 1600 cm−1. Both CTV-CMP-1 and CTV-CMP-2 showed different IR spectrum with their starting mate-rial CTV-Br3. In the spectrum of CTV-CMP-1, no-

Conjugated Porous Networks Based on Cyclotriveratrylene Building Block

Chin. J. Chem. 2013, 31, 617—623 © 2013 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.cjc.wiley-vch.de 619

Scheme 1 Synthesis of CTV-CMP-1 and CTV-CMP-2 by palladium-catalyzed C－C coupling polycondensation

BBOH

OH

HO

HO

BrO O Br Br

O

CTV-Br3

O

O

O

O

O

O

O

O

O

O

O

O

+

Pd(PPh)4, DMF,K2CO3 (2 mol/L, 16 mL)

n

(a)

CTV-CMP-1

87%

150 oC, 36 h

BrO O Br Br

O

H H

CTV-Br3

O

O

O

O

O

O

O

O

O

O

O

O

+

Pd(PPh)4, CuI, Et3N

DMF, 90 oC, 72 h

CTV-CMP-289%

(b)

n

intense peaks for B－OH bands (at 3370 cm−1) have been found and the disappearances of C－Br bonds at

521－690 cm−1 suggest the formation of the product. In the IR spectrum of CTV-CMP-2, the peak near 2205



cm−1 corresponding to the alkyne －C≡C－ stretch has been found and no intense alkynyl C－H stretch near 3300 cm−1.

By using the elemental analysis and thermogravi-metric analysis (TGA), CTV-CMP-1 and CTV-CMP-2 were explored further. While the elemental analysis of CTV-CMP-1 revealed: C 67.38, H 5.17 wt%, the theo-retical data would be: C 83.52, H 7.2 wt%; elemental analysis of CTV-CMP-2 revealed: C 73.70, H 4.97 wt%, the theoretical data would be: C 86.16, H 5.01 wt%. The low content of carbon indicates the incom-plete reaction of the polymers. There are two main rea-sons for this result: the low reactivity of bromide and the crowed structure covered the reaction site.

The thermal stability of CTV-CMP-1 and CTV-CMP-2 was analyzed by TG analysis under ni-trogen. As shown in Figure 2, CTV-CMP-1 and CTV-CMP-2 were stable before 300 ℃ under nitro-gen. The decomposition happened when temperature went above 300 ℃ while there was just a 35% weight loss when the temperature reached 900 ℃ for both of the polymers which showed their high stability. There is no evidence for distinct glass transition for these poly-mers below the thermal decomposition temperature due to the nature of their rigid structures. Moreover, CTV-CMP-1 and CTV-CMP-2 are chemically stable. They are insoluble in most of the solvents such as methanol, ethanol, THF, DMF, CH2Cl2, acetone, and even in concentrated hydrochloric acid.

Figure 2 TGA plots of CTV-CMP-1 and CTV-CMP-2 under nitrogen.

The structures of CTV-CMP-1 and CTV-CMP-2 were confirmed by 13C CP/MAS NMR (Figure 3). The solid 13C NMR spectra for the porous polymers with assignment of the resonances are shown in Figure 3. For CTV-CMP-1, there are six broad peaks at approxi-mately δ 155, 140, 130, 113, 55 and 35. Peaks at δ 55 and 35 correspond to the methylene group and methoxy group respectively; the peak at δ 155 corresponds to the substituted phenyl carbons binding with oxygen atom. Peaks at δ 140, 130 and 113 correspond to the other phenyl carbons. Similar to CTV-CMP-1, CTV-CMP-2 shows six broad peaks at δ 155, 130, 113, 93, 55 and 35.

There is obvious evidence for Sonogashira-Hagihara coupling reactions ascribed to the low intense peak at about δ 93 which corresponds to the alkynyl carbons.

To characterize the porosity of CTV-CMP-1 and CTV-CMP-2 networks, N2 adsorption isotherm was measured at 77 K. These two porous materials were stirred in dry dichloromethane for 24 h, then washed with pentane and dried under vacuum at 120 ℃ for another 24 h before N2 adsorption analysis. As shown in Figure 4, CTV-CMP-1 and CTV-CMP-2 possess the type IV nitrogen gas sorption isotherm according to the IUPAC classification.[14] This result confirms the meso porous nature of these two materials. The N2 desorption isotherm of CTV-CMP-1 and CTV-CMP-2 show the type H4 loop which associates with narrow slit-like pores. Until now, the effect of various factors on the hysteresis is not fully understood, but most people be-lieve that it associates with capillary condensation tak-ing place in the mesopores. As for CTV-CMP-1 and CTV-CMP-2, maybe the incomplete reactions result in the low degree of cross-linking and structures of these two materials being not highly rigid: these mesoporous materials undergo elastic deformation during the course of N2 sorption; that is, the networks are swelling. This is in accordance with the low specific surface area and micropore volume of CTV-CMP-1 and CTV-CMP-2 (Table 1). The BET surface areas of CTV-CMP-1 and CTV-CMP-2 are 314 cm2•g−1, and 218 cm2•g−1 which is lower than the CMPs prepared from tetrahedral mono-mers. Except for the incomplete reactions, the concave CTV has a columnar packing tendency. The extended aromatic strut enhanced the π-π interaction and flexibil-ity which lead to the higher packing ability. Pore size distribution (PSD) of CTV-CMP-1 and CTV-CMP-2 was analyzed based on the density function theory (DFT). As shown in Figure 5, CTV-CMP-1 and CTV-CMP-2 have similar PSDs with dominant pore width at 0.7 nm. Previous work showed that the pore width of CTC-PIM network is around 0.6 nm which is related to the internal dimensions of the bowl-shaped CTV subunit.[11a] The result suggested that pore size distribution within microporous networks can be tuned by the choice of monomer precursor. In CTV-CMP-1 and CTV-CMP-2, as the length of the monomer linker increases, the overall micropore volume falls from 0.142 cm3•g−1 to 0.032 cm3•g−1. This trend is similar with the previous reported CMP which indicates the structure property of the porous material could be in-fluenced by the strut.[6c,6j]

Hydrogen adsorptions for CTV-CMP-1 and CTV-CMP-2 were measured at 77 K up to a pressure of 1.13 bar (Figure 6). At 1.13 bar, CTV-CMP-1 and CTV-CMP-2 can absorb 0.81 wt% and 0.51 wt% of H2. Though no saturation was reached, and these two po-rous materials were expected higher hydrogen uptake with increasing pressure, while the hydrogen adsorption at low pressure is below the reported networks.[6]

Compared with CTV-CMP-1, CTV-CMP-2 has



Figure 3 13C CP/MAS NMR spectra of CTV-CMP-1 and CTV-CMP-2.

Figure 4 Nitrogen adsorption-desorption isotherms of CTV- CMP-1 and CTV-CMP-2 measured at 77 K (the adsorption and desorption branches are labeled with solid and open symbols, respectively).

Figure 5 Pore size distribution plots of CTV-CMP-1 and CTV-CMP-2.

lower specific surface area and contains smaller micro-

Table 1 Porosity and hydrogen uptake capacities of CTV-CMP-1 and CTV-CMP-2

Polymer SBET

a/ (m2•g−1)

Smicrob/

(m2•g−1) Vtotal

c/ (cm3•g−1)

Vmicrod/

(cm3•g−1)Hydrogen uptakee/wt%

CTV-CMP-1 314 168 0.370 0.143 0.81

CTV-CMP-2 218 53 0.345 0.032 0.51 a Specific surface area calculated from the nitrogen adsorption isotherm using the BET method. b The specific surface area for the micropores calculated from the nitrogen adsorption isotherm using the t-plot method. c Total pore volume at p/p0 0.99. d Mi-cropore volume derived using the t-plot method based on the Halsey thickness equation. e Data are obtained at 1.13 bar and 77 K.

Figure 6 H2 adsorption isotherms of CTV-CMP-1 and CTV-CMP-2 measured at 77 K.

pore volume which is consistent with its lower hydrogen uptake. But previous work showed that specific surface



area is not the only criterion for hydrogen adsorption[15] and pores of diameter in the range of 0.6－0.8 nm are optimal for hydrogen physisorption at low pressures for various microporous materials.[16] That could be one reason for the relatively high hydrogen adsorption for CTV-CMP-2, while we suspected that there could be the ultramicropore in CTV-CMP-2 which can not be detected in nitrogen adsorption. Moreover, these two conjugated porous networks possess higher H2 adsorp-tion ability than our previously reported POPs prepared by Click reaction.[12] SEM images show the amorphous structure of CTV-CMP-1 and CTV-CMP-2 in Figure 7. SEM images display that both of the polymers consist of relatively uniform solid submicrometer spheres. SEM images revealed the intense aggregation of solid sphere which could be the reason for low specific surface area and pore volume in CTV-CMP-1 and CTV-CMP-2.

Figure 7 SEM images of CTV-CMP-1 and CTV-CMP-2.

Conclusions In conclusion, we synthesized CTV-CMP-1 and

CTV-CMP-2 via Suzuki and Sonogashira-Hagihara coupling reactions which showed both microporous and mesoporous characteristics. The rigid porous networks are confirmed by FT-IR, 13C CP/MAS NMR, and ele-mental analysis. TG analysis showed high stability of CTV-CMP-1 and CTV-CMP-2. The BET specific surface areas of CTV-CMP-1 and CTV-CMP-2 are 314 and 218 cm2•g−1 respectively. Gravimetric hydrogen adsorption isotherms of CTV-CMP-1 and CTV- CMP-2 showed their adsorption capacities for hydrogen are 0.81 wt% and 0.51 wt% at 1.13 bar and 77 K. Ag-gregation in the conjugated networks may be responsi-ble for the low specific surface areas as well as the low microporous volume. As these materials resemble acti-vated carbons in structure, CTV-CMP-1 and CTV- CMP-2 could be potentially used in gas separation and organic compound adsorption.

Acknowledgement This work was supported by the National Natural

Science Foundation of China (No. 20932004), the Ma-jor State Basic Research Development Program of China (No. 2011CB932501), and the Chinese Academy of Sciences.

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(Lu, Y.)

Conjugated Porous Networks Based on Cyclotriveratrylene Building Block for Hydrogen Adsorption

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