Abstract
A shape-persistent dendritic molecule, tris(4-(2,7-dibromo-9-phenyl-9-fluoren-9-yl)phenyl)amine (TF-6Br), has been readily synthesized in high yield through a concise Friedel-Crafts reaction from triphenylamine and 2,7-dibromo(9-phenyl-fluoren-9-ol). It was further employed as the key building block to achieve the synthesis of conjugated porous polymer via Sonogashira coupling with 1,4-diethynylbenzene. Under experimental reaction conditions, the resulting porous polymer shows exceptionally nanotubular morphology, which further allows for a template-free synthesis of porous carbon nanotubes via thermal treatment at high temperature. The obtained nitrogen-doped carbon nanotubes feature with an improved porosity and high surface area.
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Wu XF, Xu BW, Tong H, Wang LX. Phosphonate-functionalized polyfluorene film snsors for sensitive detection of Iron(III) in both organic and aqueous media. Macromolecules, 2010, 43(21), 8917–8923
Huang F, Hou LT, Wu HB, Wang XH, Shen HL, Cao W, Yang W, Cao Y. High-efficiency, environment-friendly electroluminescent polymers with stable high work function metal as a cathode: Green- and yellow-emitting conjugated polyfluorene polyelectrolytes and their neutral precursors. J Am Chem Soc, 2004, 126(31):9845–9853
Zhuang XD, Chen Y, Li BX, Ma DG, Zhang B, Li YX. Polyfluorene-based push-pull type functional materials for write-once-read-many-times memory devices. Chem Mater, 2010, 22(15):4455–4461
Chen Q, Wang JX, Wang Q, Bian N, Li ZH, Yan CG, Han BH. Spiro(fluorene-9,9′-xanthene)-based porous organic polymers: Preparation, porosity, and exceptional hydrogen uptake at low pressure. Macromolecules, 2011, 44(20):7987–7993
Ritter N, Senkovska I, Kaskel S, Weber J. Intrinsically microporous poly(imide)s: Structure-porosity relationship studied by gas sorption and X-ray scattering. Macromolecules, 2011, 44(7): 2025–2033.
Feng X, Liang Y, Zhi L, Thomas A, Wu D, Lieberwirth I, Kolb U, Müllen K. Synthesis of microporous carbon nanofibers and nanotubes from conjugated polymer network and evaluation in electrochemical capacitor. Adv Funct Mater, 2009, 19(13):2125–2129
Schwab MG, Fassbender B, Spiess HW, Thomas A, Feng X, Müllen K. Catalyst-free preparation of melamine-based microporous polymer networks through Schiff base chemistry. J Am Chem Soc, 2009, 131(21):7216–7217
Zhang B, Chen Y, Liu G, Xu LQ, Chen JN, Zhu CX, Neoh KG, Kang ET. Push-pull archetype of reduced graphene oxide functionalized with polyfluorene for nonvolatile rewritable memory. J Polym Sci Part A-Polym Chem, 2012, 50(2):378–387
Hu SJ, Zou JH, Zhou GJ, Li DY, Wu HB, Su SJ, Wong WY, Yang W, Peng JB, Cao Y. Highly efficient pure white polymer light-emitting devices based on poly(N-vinylcarbazole) doped with blue and red phosphorescent dyes. Sci China Chem, 2011, 54(4):671–677
Duan CH, Wang CD, LIU SJ, Huang F, Choy CHW, CAO Y. Two-dimensional like conjugated copolymers for high efficiency bulk-heterojunction solar cell application: Band gap and energy level engineering. Sci China Chem, 2011, 54(4):685–694
Xie LH, Hou XY, Hua YR, Tang C, Liu F, Fan QL, Huang W. Facile synthesis of complicated 9,9-diarylfluorenes based on BF3 center dot Et2O-mediated Friedel-Crafts reaction. Org Lett, 2006, 8(17):3701–3704
Liu F, Lai WY, Tang C, Wu HB, Chen QQ, Peng B, Wei W, Huang W, Cao Y. Synthesis and characterization of pyrene-centered starburst oligofluorenes. Macromol Rap Comm, 2008, 29(8):659–664
Xie LH, Ling QD, Hou XY, Huang W. An effective Friedel-Crafts postfunctionalization of poly(N-vinylcarbazole) to tune carrier transportation of supramolecular organic semiconductors based on pi-stacked polymers for nonvolatile flash memory cell. J Am Chem Soc, 2008, 130(7):2120–2121
Li C, Liu MY, Pschirer NG, Baumgarten M, Mullen K. Polyphenylene-based materials for organic photovoltaics. Chem Rev, 2010, 110(11):6817–6855
Farinola GM, Ragni R. Electroluminescent materials for white organic light emitting diodes. Chem Soc Rev, 2011, 40(7):3467–3482
Campbell N, Temple AF. Synthesis of indenoquinolines. J Chem Soc, 1957, 207–212
Tour JM, Wu R, Schumm JS. Approaches to orthogonally fused conducting polymers for molecular electronics. J Am Chem Soc, 1990, 112(14):5663–5665
Bouffard J, Swager TM. Fluorescent conjugated polymers that incorporate substituted 2,1,3-benzooxadiazole and 2,1,3-benzothiadiazole units. Macromolecules, 2008, 41(15), 5559–5562
Schmidt J, Werner M, Thomas A. Conjugated microporous polymer networks via Yamamoto polymerization. Macromolecules, 2009, 42(13):4426–4429
Weber J, Thomas A. Toward stable interfaces in conjugated polymers: Microporous poly(p-phenylene) and poly (phenyleneethynylene) based on a spirobifluorene building block. J Am Chem Soc, 2008, 130(20):6334–6335
Cao XY, Zhou XH, Zi H, Pei J. Novel blue-light-emitting truxene-containing hyperbranched and zigzag type copolymers: Synthesis, optical properties, and investigation of thermal spectral stability. Macromolecules, 2004, 37(24):8874–8882
Sun MH, Li J, Li BS, Fu YQ, Bo ZS. Toward high molecular weight triphenylamine-based hyperbranched polymers. Macromolecules, 2005, 38(7):2651–2658
Li B, Li J, Fu Y, Bo Z. Porphyrins with four monodisperse oligofluorene arms as efficient red light-emitting materials. J Am Chem Soc, 2004, 126(11):3430–3431
Liu XM, He C, Huang J, Xu J. Highly efficient blue-light-emitting glass-forming molecules based on tetraarylmethane/silane and fluorene: Synthesis and thermal, optical, and electrochemical properties. Chem Mater, 2004, 17(2):434–441
Liu XM, Lin T, Huang J, Hao XT, Ong KS, He C. Hyperbranched blue to red light-emitting polymers with tetraarylsilyl cores: Synthesis, optical and electroluminescence properties, and ab initio modeling studies. Macromolecules, 2005, 38(10):4157–4168
Kolel-Veetil MK, Dominguez DD, Klug CA, Keller TM. Hydrosilated dendritic networks of POSS cores and diacetylene linkers. Macromolecules, 2009, 42(12):3992–4001
Dawson R, Laybourn A, Clowes R, Khimyak YZ, Adams DJ, Cooper AI. Functionalized conjugated microporous polymers. Macromolecules, 2009, 42(22):8809–8816
Zhu XJ, Holliday BJ. Electropolymerization of a ruthenium(II) bis(pyrazolyl)pyridine complex to form a novel Ru-containing conducting metallopolymer. Macromol Rap Commun, 2010, 31(9–10):904–909
Colquhoun HM, Sestiaa LG, Williams DJ, Zolotukhin M G. Macro-ring-functionalised poly(ether ether ketone): A new molecular architecture for aromatic polymers. Macromol Rap Commun, 2002, 23(10–11):634–638
Lei T, Luo J, Wang L, Ma YG, Wang J, Cao Y, Pei J. Highly stable blue light-emitting materials with a three-dimensional architecture: Improvement of charge injection and electroluminescence performance. New J Chem, 2010, 34(4):699–707
Luo J, Lei T, Wang L, Ma YG, Cao Y, Wang J, Pei J. Highly fluorescent rigid supramolecular polymeric nanowires constructed through multiple hydrogen bonds. J Am Chem Soc, 2009, 131(6):2076–2077
Luo J, Zhou Y, Niu ZQ, Zhou QF, Ma YG, Pei J. Three-dimensional architectures for highly stable pure blue emission. J Am Chem Soc, 2007, 129(37):11314–11315
Jones JTA, Hasell T, Wu X, Bacsa J, Jelfs KE, Schmidtmann M, Chong SY, Adams DJ, Trewin A, Schiffman F, Cora F, Slater B, Steiner A, Day GM, Cooper AI. Modular and predictable assembly of porous organic molecular crystals. Nature, 2011, 474(7351):367–371
Johnson SA, Brigham ES, Ollivier PJ, Mallouk TE. Effect of micropore topology on the structure and properties of zeolite polymer replicas. Chem Mater, 1997, 9(11):2448–2458
White RJ, Antonietti M, Titirici MM. Naturally inspired nitrogen doped porous carbon. J Mater Chem, 2009, 19(45):8645–8650
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Recommended by Prof. YAN Deyue (Shanghai Jiao Tong University)
ZHANG Fan (left), received his B.Eng. degree in electrochemistry from Shanghai Jiao Tong University in 1991, and his Ph.D. in organic chemistry from Jilin University in 2000. After more than eight years of research experience in Germany and the United States, he was promoted to a Research Professor in School of Chemistry and Chemical Engineering of Shanghai Jiao Tong University, China. His research interests span from organometallic catalysis, olefin polymerization to organic π-conjugated functional materials for energy conversion and storage.
FENG Xinliang (center), after obtaining his Master’s degree in organic chemistry from Shanghai Jiao Tong University in March 2004, joined the group of Prof. K. Müllen at the Max Planck Institute for polymer research (MPIP) and obtained his Ph.D. in April 2008. Since December 2007, he has been a group leader at MPIP. Since June 2010, he has been a professor of Shanghai Jiao Tong University and was appointed as director for the Institute of Advanced Organic Materials. His current scientific interests include graphene, two-dimensional nanomaterials, organic conjugated materials, carbon-rich molecules and materials for electronic and energy-related applications.
ZHUANG Xiaodong (right), received his Ph.D. degree from East China University of Science and Technology in 2011 and was supervised by Prof. Yu Chen. He is currently a postdoctoral fellow in Shanghai Jiao Tong University (co-supervisor: Prof. Xinliang Feng). He has published 20 articles in the international journals such as Adv. Mater., J. Am. Chem. Soc., Adv. Funct. Mater., Chem. Mater. and others. His main research interest includes polymer synthesis, graphene chemistry, and porous polymers/carbons for resistive memory, energy storage and electrochemical catalysis.
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Zhuang, X., Zhang, Y., Cao, C. et al. One-step preparation of novel conjugated porous polymer with tubular structure. Sci. China Chem. 56, 1112–1118 (2013). https://doi.org/10.1007/s11426-013-4879-8
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DOI: https://doi.org/10.1007/s11426-013-4879-8