구리 촉매화 클릭 반응을 통한 새로운 공액 미세 다공성 고분자의 합성 및 이산화탄소 포집 능력

박정원; 이창연; Jungwon Park; Chang Yeon Lee

Polymer(Korea), Vol.42, No.3, 371-376, May, 2018

DOI10.7317/pk.2018.42.3.371 Export Citation

구리 촉매화 클릭 반응을 통한 새로운 공액 미세 다공성 고분자의 합성 및 이산화탄소 포집 능력

Synthesis of New Conjugated Microporous Polymers via Copper-catalyzed Click Reaction and Their CO2 Capture Ability

박정원, 이창연^†

인천대학교 에너지화학공학과

Jungwon Park, and Chang Yeon Lee^†

Department of Energy and Chemical Engineering, Incheon National University, Incheon 22012, Korea

E-mail:

초록

본 연구에서는 1,3,6,8-tetraethynylpyrene(1)과 azido 그룹을 포함하는 1,4-diazidobenzene(2), 4.4'-diazidobiphenyl (3)간의 클릭 반응을 통하여 공액 미세기공 고분자, CMP-1과 CMP-2를 합성하였다. 합성된 폴리머들은 FTIR과 고체상 13C NMR을 통해 그들의 구조를 분석하였고, N2-흡탈착 등온선 및 CO2 흡착 등온선을 통해 표면적 및 이산화탄소 흡착 능력을 측정하였다. 분자의 길이가 더 긴 단량체 3으로 합성된 CMP-2에서 BET 표면적이 증가되고 기공 크기가 감소되는 것이 관찰되었으며 이산화탄소 흡착 결과 298 K에서는 CMP-1과 CMP-2가 비슷한 흡착량을 보였으나 273 K에서는 CMP-2의 흡착량이 CMP-1에 비해 약 1.5배 증가됨이 관찰되었다. CMP-2의 우월한 이산화탄소 흡착성능은 높은 표면적과 이산화탄소 흡착에 적합한 0.4~0.8 nm의 미세 기공의 존재에 기인한다.

In this study, conjugated microporous polymer, CMP-1 and CMP-2, were synthesized via the copper-catalyzed click reaction between 1,3,6,8-tetraethynylpyrene(1) and 1,4-diazidobenzene(2) or 4,4'-diazidobiphenyl(3). The obtained polymers were characterized by FTIR and solid state 13C NMR, and their surface area and carbon dioxide adsorption capacities were measured by N2-adsorption/desorption isotherms and CO2 adsorption isotherms, respectively. The BET surface area was increased and the pore size was decreased in the CMP-2 which is originated from the monomer 3 having a longer molecular length. CMP-1 and CMP-2 exhibited similar CO2 adsorption capacities at 298 K, 1 bar but CMP-2 displayed superior CO2 adsorption ability compared with CMP-1 at 273 K. The enhanced CO2 adsorption ability of CMP- 2 can be attributed to its high surface areas and appropriate pore diameter to capture CO2 molecules.

Keywords:CO2 capture;conjugated microporous polymer;click-reaction;metal-organic frameworks;pore size

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[Referenced By]

[1] Plaza MG, Garcia S, Rubiera F, Pis JJ, Pevida C, Chem. Eng. J., 163(1-2), 41 (2010)

[2] Wang Y, Levan MD, J. Chem. Eng. Data, 54(10), 2839 (2009)

[3] Zhang Z, Yao ZZ, Xiang S, Chen B, Energy Environ. Sci., 7, 2868 (2014)

[4] Jiang JX, Su F, Trewin Z, Wood CD, Campbell NL, Niu H, Dickinson C, Ganin AY, Rosseinsky MJ, Khimyak YZ, Cooper AI, Angew. Chem.-Int. Edit., 46, 8574 (2007)

[5] Lasseuguette E, Carta M, Brandani S, Ferrari MC, Int. J. Greenh. Gas Control, 50, 93 (2016)

[6] Martin CF, Stockel E, Clowes R, Adams DJ, Cooper AI, Pis JJ, Rubiera F, Pevida C, J. Mater. Chem., 21, 5475 (2011)

[7] Zeng YF, Zou RQ, Zhao YL, Adv. Mater., 28(15), 2855 (2016)

[8] Dawson R, Adams DJ, Cooper AI, Chem. Sci., 2, 1173 (2011)

[9] Ma H, Ren H, Zou X, Meng S, Sun F, Zhu G, Polym. Chem., 5, 144 (2014)

[10] Yu M, Wang X, Yang X, Zhao Y, Jiang JX, Polym. Chem., 6, 3217 (2015)

[11] Park KC, Cho J, Lee CY, RSC Adv., 6, 75478 (2016)

[12] Kou Y, Xu Y, Guo Z, Jiang D, Angew. Chem.-Int. Edit., 50, 8753 (2011)

[13] Chen L, Honsho Y, Seki S, Jiang DL, J. Am. Chem. Soc., 132(19), 6742 (2010)

[14] Gu C, Chen YC, Zhang ZB, Xue SF, Sun SH, Zhang K, Zhong CM, Zhang HH, Pan YY, Lv Y, Yang YQ, Li FH, Zhang SB, Huang F, Ma YG, Adv. Mater., 25(25), 3443 (2013)

[15] Zhang K, Kopet.ki D, Seeberger PH, Antonietti M, Vilela F, Angew. Chem.-Int. Edit., 52, 1432 (2013)

[16] Jin Y, Zhu Y, Zhang W, Cryst. Eng. Comm., 15, 1484 (2013)

[17] Cordes EH, Jencks WP, J. Am. Chem. Soc., 84, 832 (1962)

[18] Fisher MJ, Myers CD, Joglar J, Chen SH, Danishefsky SJ, J. Org. Chem., 56, 5826 (1991)

[19] Langecker J, Rehahn M, Macromol. Chem. Phys., 209, 258 (2008)

[20] Suzuki A, Chem. Commun., 4759 (2005).

[21] Suzuki A, Angew. Chem.-Int. Edit., 50, 6723 (2011)

[22] Lagona J, Fettinger JC, Isaacs L, J. Org. Chem., 70, 10381 (2005)

[23] Chinchilla R, Najera C, Chem. Soc. Rev., 40, 5084 (2011)

[24] Liu C, Zhang H, Shi W, Lei AW, Chem. Rev., 111(3), 1780 (2011)

[25] Shi W, Liu C, Lei A, Chem. Soc. Rev., 40, 2761 (2011)

[26] Barner-Kowollik C, Prez FED, Espeel P, Hawker CJ, Junkers T, Schlaad H, Camp WV, Angew. Chem.-Int. Edit., 50, 60 (2011)

[27] Liang L, Astruc D, Coord. Chem. Rev., 255, 2933 (2011)

[28] Venkataramana G, Sankararaman S, Eur. J. Org. Chem., 2005, 4162 (2005)

[29] Luo L, Frisbie CD, J. Am. Chem. Soc., 132(26), 8854 (2010)

[30] Yuan WZ, Mahtab F, Gong Y, Yu ZQ, Lu P, Tang Y, Lam JWY, Zhu C, Tang BZ, J. Mater. Chem., 22, 10472 (2012)

[31] Weber J, Thomas A, J. Am. Chem. Soc., 130(20), 6334 (2008)

[32] Weber J, Antonietti M, Thomas A, Macromolecules, 41(8), 2880 (2008)

[33] Nugent P, Belmabkhout Y, Burd SD, Cairns AJ, Luebke R, Forrest K, Pham T, Ma SQ, Space B, Wojtas L, Eddaoudi M, Zaworotko MJ, Nature, 495(7439), 80 (2013)