Controlled synthesis of ortho, para-alternating linked polyarenes via catalyst-transfer Suzuki coupling polymerization

Zhang, Hong -Hai; Zhu, Yu -Xing; Wang, Weiyu; Zhu, Jiahua; Bonnesen, Peter V.; Hong, Kunlun

doi:10.1039/C8PY00070K

Title: Controlled synthesis of ortho, para-alternating linked polyarenes via catalyst-transfer Suzuki coupling polymerization

Journal Article · Fri Apr 27 00:00:00 EDT 2018 · Polymer Chemistry

DOI:https://doi.org/10.1039/C8PY00070K· OSTI ID:1523761

Zhang, Hong -Hai ^[1]; Zhu, Yu -Xing ^[1];

^[2];

^[2]

Nanjing Tech Univ. (Nanjing Tech), Nanjing (People's Republic of China)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

A novel class of ortho, para-alternating linked polyarenes is synthesized via catalyst-transfer Suzuki coupling polymerization with Pd₂(dba)₃/t-Bu₃P/p-BrC₆H₄COPh as initiator. Through a series of kinetic studies and MALDI-TOF analysis, the polymerization is shown to proceed in a chain-growth manner. The optical and thermal properties for the ortho, para-alternating linked polyarenes exhibit unusual molecular weight dependence. Thus, the polymer with lower molecular weight (M_n = 6300 g mol^–1) emits green fluorescence whereas the one with higher molecular weight (M_n = 13 800 g mol^–1) emits blue fluorescence under UV (λ = 360 nm) irradiation. Furthermore, an all-conjugated block copolymer containing a polyfluorene block and the ortho, para-alternating linked block is also successfully prepared, in a one-pot procedure. These results can provide a pathway to obtain polyarenes with precisely controlled structures, hence, desirable properties.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC05-00OR22725; LOIS# 7938

OSTI ID:: 1523761

Alternate ID(s):: OSTI ID: 1435664

Journal Information:: Polymer Chemistry, Vol. 9, Issue 24; ISSN 1759-9954

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 6 works

Citation information provided by
Web of Science

References (42)

Controlled Pd(0)/ t -Bu ₃ P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with PhPd( t -Bu ₃ P)I or Pd ₂ (dba) ₃ / t -Bu ₃ P/ArI as the Initiator Zhang, Hong-Hai; Xing, Chun-Hui; Hu, Qiao-Sheng Journal of the American Chemical Society, Vol. 134, Issue 32 https://doi.org/10.1021/ja302745t	journal	August 2012
Construction of Donor–Acceptor Polymers via Cyclopentannulation of Poly(arylene ethynylene)s Zhu, Xinju; Bheemireddy, Sambasiva R.; Sambasivarao, Somisetti V. Macromolecules, Vol. 49, Issue 1 https://doi.org/10.1021/acs.macromol.5b02061	journal	December 2015
Chain-Growth Suzuki Polymerization of n-Type Fluorene Copolymers Elmalem, Einat; Kiriy, Anton; Huck, Wilhelm T. S. Macromolecules, Vol. 44, Issue 22 https://doi.org/10.1021/ma201934q	journal	November 2011
Folding of ortho -Phenylenes Hartley, C. Scott Accounts of Chemical Research, Vol. 49, Issue 4 https://doi.org/10.1021/acs.accounts.6b00038	journal	March 2016
Synthesis of Highly Fluorescent All-Conjugated Alternating Donor–Acceptor (Block) Copolymers via GRIM Polymerization Govaerts, Sanne; Verstappen, Pieter; Penxten, Huguette Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01389	journal	August 2016
Aryne Polymerization Enabling Straightforward Synthesis of Elusive Poly( ortho -arylene)s Mizukoshi, Yoshihide; Mikami, Koichiro; Uchiyama, Masanobu Journal of the American Chemical Society, Vol. 137, Issue 1 https://doi.org/10.1021/ja5112207	journal	December 2014
Conjugated Polymers with Repeated Sequences of Group 16 Heterocycles Synthesized through Catalyst-Transfer Polycondensation Tsai, Chia-Hua; Fortney, Andria; Qiu, Yunyan Journal of the American Chemical Society, Vol. 138, Issue 21 https://doi.org/10.1021/jacs.6b01916	journal	May 2016
Chain-Growth Polymerization for the Synthesis of Polyfluorene via Suzuki−Miyaura Coupling Reaction from an Externally Added Initiator Unit Yokoyama, Akihiro; Suzuki, Hirofumi; Kubota, Yasuhiro Journal of the American Chemical Society, Vol. 129, Issue 23 https://doi.org/10.1021/ja070313v	journal	June 2007
Controlled Synthesis of an Alternating Donor–Acceptor Conjugated Polymer via Kumada Catalyst-Transfer Polycondensation Todd, Alexander D.; Bielawski, Christopher W. ACS Macro Letters, Vol. 4, Issue 11 https://doi.org/10.1021/acsmacrolett.5b00505	journal	October 2015
o -Phenylene Octamers as Surface Modifiers for Homeotropic Columnar Ordering of Discotic Liquid Crystals Kajitani, Takashi; Suna, Yuki; Kosaka, Atsuko Journal of the American Chemical Society, Vol. 135, Issue 39 https://doi.org/10.1021/ja4087853	journal	September 2013
Enhanced Helical Folding of ortho -Phenylenes through the Control of Aromatic Stacking Interactions Mathew, Sanyo; Crandall, Laura A.; Ziegler, Christopher J. Journal of the American Chemical Society, Vol. 136, Issue 47 https://doi.org/10.1021/ja509902m	journal	November 2014
Dimensional Evolution of Polyphenylenes: Expanding in All Directions Hammer, Brenton A. G.; Müllen, Klaus Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00515	journal	December 2015
Synthesis of poly(1,10-phenanthroline-5,6-diyl)s having a π-stacked, helical conformation Yang, Weixi; Nakano, Tamaki Chemical Communications, Vol. 51, Issue 97 https://doi.org/10.1039/C5CC07005H	journal	January 2015
Mechanistic Investigation of Catalyst-Transfer Suzuki-Miyaura Condensation Polymerization of Thiophene-Pyridine Biaryl Monomers with the Aid of Model Reactions Tokita, Yu; Katoh, Masaru; Ohta, Yoshihiro Chemistry - A European Journal, Vol. 22, Issue 48 https://doi.org/10.1002/chem.201603581	journal	October 2016
Highly Efficient Benzannulation of Poly(phenylene ethynylene)s Arslan, Hasan; Saathoff, Jonathan D.; Bunck, David N. Angewandte Chemie International Edition, Vol. 51, Issue 48 https://doi.org/10.1002/anie.201206964	journal	October 2012
Exciton Diffusion in Conjugated Polymers: From Fundamental Understanding to Improvement in Photovoltaic Conversion Efficiency Tamai, Yasunari; Ohkita, Hideo; Benten, Hiroaki The Journal of Physical Chemistry Letters, Vol. 6, Issue 17 https://doi.org/10.1021/acs.jpclett.5b01147	journal	August 2015
Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers Thomas, Samuel W.; Joly, Guy D.; Swager, Timothy M. Chemical Reviews, Vol. 107, Issue 4 https://doi.org/10.1021/cr0501339	journal	April 2007
t -Bu ₃ P-Coordinated 2-Phenylaniline-Based Palladacycle Complex/ArBr as Robust Initiators for Controlled Pd(0)/ t -Bu ₃ P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers Zhang, Hong-Hai; Peng, Wei; Dong, Jie ACS Macro Letters, Vol. 5, Issue 6 https://doi.org/10.1021/acsmacrolett.6b00230	journal	May 2016
Transformation of Step-Growth Polymerization into Living Chain-Growth Polymerization Yokozawa, Tsutomu; Ohta, Yoshihiro Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00393	journal	November 2015
Three-Way-Switchable ( Right / Left / OFF ) Selective Reflection of Circularly Polarized Light on Solid Thin Films of Helical Polymer Blends Nagata, Yuuya; Uno, Makoto; Suginome, Michinori Angewandte Chemie International Edition, Vol. 55, Issue 25 https://doi.org/10.1002/anie.201602035	journal	April 2016
Formal Aryne Polymerization: Use of [2.2.1]Oxabicyclic Alkenes as Aryne Equivalents Ito, Shingo; Takahashi, Keisuke; Nozaki, Kyoko Journal of the American Chemical Society, Vol. 136, Issue 21 https://doi.org/10.1021/ja502073k	journal	May 2014
Graphene Nanoribbons by Chemists: Nanometer-Sized, Soluble, and Defect-Free Dössel, Lukas; Gherghel, Lileta; Feng, Xinliang Angewandte Chemie International Edition, Vol. 50, Issue 11 https://doi.org/10.1002/anie.201006593	journal	January 2011
Matchmaking in Catalyst-Transfer Polycondensation: Optimizing Catalysts based on Mechanistic Insight Leone, Amanda K.; McNeil, Anne J. Accounts of Chemical Research, Vol. 49, Issue 12 https://doi.org/10.1021/acs.accounts.6b00488	journal	November 2016
Helical Poly(5-alkyl-2,3-thiophene)s: Controlled Synthesis and Structure Characterization Zhang, Hong-Hai; Ma, Chuanxu; Bonnesen, Peter V. Macromolecules, Vol. 49, Issue 13 https://doi.org/10.1021/acs.macromol.6b01233	journal	June 2016
Sequence-defined oligo( ortho -arylene) foldamers derived from the benzannulation of ortho (arylene ethynylene)s Lehnherr, Dan; Chen, Chen; Pedramrazi, Zahra Chemical Science, Vol. 7, Issue 10 https://doi.org/10.1039/C6SC02520J	journal	January 2016
ortho -Phenylenes: Unusual Conjugated Oligomers with a Surprisingly Long Effective Conjugation Length He, Jian; Crase, Jason L.; Wadumethrige, Shriya H. Journal of the American Chemical Society, Vol. 132, Issue 39 https://doi.org/10.1021/ja106050s	journal	October 2010
Synthesis, Structure, and Properties of α,β‐Linked Oligothiazoles with Controlled Sequence Nakashima, Takuya; Imamura, Kazuhiko; Yamamoto, Kyohei Chemistry – A European Journal, Vol. 20, Issue 42 https://doi.org/10.1002/chem.201403791	journal	September 2014
Suzuki Polycondensation: Polyarylenes à la Carte Sakamoto, Junji; Rehahn, Matthias; Wegner, Gerhard Macromolecular Rapid Communications, Vol. 30, Issue 9-10 https://doi.org/10.1002/marc.200900063	journal	May 2009
Catalyst-Transfer Polycondensation. Mechanism of Ni-Catalyzed Chain-Growth Polymerization Leading to Well-Defined Poly(3-hexylthiophene) Miyakoshi, Ryo; Yokoyama, Akihiro; Yokozawa, Tsutomu Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja0556880	journal	December 2005
Twisted Macrocycles with Folded ortho -Phenylene Subunits Kinney, Zacharias J.; Hartley, C. Scott Journal of the American Chemical Society, Vol. 139, Issue 13 https://doi.org/10.1021/jacs.7b00149	journal	March 2017
Asymmetric Synthesis of Helical Poly(quinoxaline-2,3-diyl)s by Palladium-Mediated Polymerization of 1,2-Diisocyanobenzenes: Effective Control of the Screw-Sense by a Binaphthyl Group at the Chain-End Ito, Yoshihiko; Miyake, Toshiyuki; Hatano, Seiji Journal of the American Chemical Society, Vol. 120, Issue 46 https://doi.org/10.1021/ja982500m	journal	November 1998
Synthesis and Helical Structure of Oligo(quinoline-2,3-diyl)s Suginome, Michinori; Noguchi, Hiroyoshi; Murakami, Masahiro Chemistry Letters, Vol. 36, Issue 8 https://doi.org/10.1246/cl.2007.1036	journal	August 2007
Suzuki–Miyaura catalyst-transfer polycondensation with Pd(IPr)(OAc) ₂ as the catalyst for the controlled synthesis of polyfluorenes and polythiophenes Sui, Aiguo; Shi, Xincui; Tian, Hongkun Polym. Chem., Vol. 5, Issue 24 https://doi.org/10.1039/C4PY00917G	journal	January 2014
Organic and Polymeric Semiconductors Enhanced by Noncovalent Conformational Locks Huang, Hui; Yang, Lei; Facchetti, Antonio Chemical Reviews, Vol. 117, Issue 15 https://doi.org/10.1021/acs.chemrev.7b00084	journal	July 2017
β-Oligofurans Fallon, Thomas; Willis, Anthony C.; Rae, A. David Chemical Science, Vol. 3, Issue 6 https://doi.org/10.1039/c2sc20130e	journal	January 2012
Controlled Pd(0)/ t -Bu ₃ P-Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with ArPd( t -Bu ₃ P)X or Pd ₂ (dba) ₃ / t -Bu ₃ P/ArX as the Initiator Zhang, Hong-Hai; Xing, Chun-Hui; Hu, Qiao-Sheng Macromolecules, Vol. 48, Issue 4 https://doi.org/10.1021/ma502521u	journal	January 2015
Molecular Weight Dependence of the Morphology in P3HT:PCBM Solar Cells Liu, Feng; Chen, Dian; Wang, Cheng ACS Applied Materials & Interfaces, Vol. 6, Issue 22 https://doi.org/10.1021/am505283k	journal	October 2014
Redox-responsive molecular helices with highly condensed π-clouds Ohta, Eisuke; Sato, Hiroyasu; Ando, Shinji Nature Chemistry, Vol. 3, Issue 1 https://doi.org/10.1038/nchem.900	journal	November 2010
Three-Way-Switchable ( Right / Left / OFF ) Selective Reflection of Circularly Polarized Light on Solid Thin Films of Helical Polymer Blends Nagata, Yuuya; Uno, Makoto; Suginome, Michinori Angewandte Chemie, Vol. 128, Issue 25 https://doi.org/10.1002/ange.201602035	journal	April 2016
Chemical Sensors Based on Amplifying Fluorescent Conjugated Polymers Thomas, Samuel W. III; Joly, Guy D.; Swager, Timothy M. ChemInform, Vol. 38, Issue 31 https://doi.org/10.1002/chin.200731221	journal	July 2007
Graphene Nanoribbons by Chemists: Nanometer-Sized, Soluble, and Defect-Free Dössel, Lukas; Gherghel, Lileta; Feng, Xinliang Angewandte Chemie, Vol. 123, Issue 11 https://doi.org/10.1002/ange.201006593	journal	January 2011
Highly Efficient Benzannulation of Poly(phenylene ethynylene)s Arslan, Hasan; Saathoff, Jonathan D.; Bunck, David N. Angewandte Chemie, Vol. 124, Issue 48 https://doi.org/10.1002/ange.201206964	journal	October 2012

Cited By (2)

Intramolecular Catalyst Transfer over Sterically Hindered Arenes in Suzuki Cross‐Coupling Reactions Zhu, Yu‐Xing; Li, En‐Ci; Shen, Kang Asian Journal of Organic Chemistry, Vol. 8, Issue 8 https://doi.org/10.1002/ajoc.201900228	journal	July 2019
Conjugated oligomers with alternating heterocycles from a single monomer: synthesis and demonstration of electroluminescence Urrego-Riveros, Sara; Bremer, Matthias; Hoffmann, Jonas Organic Chemistry Frontiers, Vol. 6, Issue 21 https://doi.org/10.1039/c9qo00947g	journal	January 2019

Figures / Tables (4)

Similar Records

Controlled Pd(0)/t Bu3P Catalyzed Suzuki Cross-Coupling Polymerization of AB-Type Monomers with ArPd(t Bu3P)X or Pd2(dba)3/t Bu3P/ArX as the Initiator

Journal Article · Thu Feb 05 00:00:00 EST 2015 · Macromolecules · OSTI ID:1523761

Zhang, Honghai; Xing, Chun-Hui; Hu, Qiao-Sheng; +1 more

Helical Poly(5-alkyl-2,3-thiophene)s: Controlled Synthesis and Structure Characterization

Journal Article · Tue Jul 12 00:00:00 EDT 2016 · Macromolecules · OSTI ID:1523761

Zhang, Hong-Hai; Ma, Chuanxu; Bonnesen, Peter V.; +7 more

Precise synthesis of thermoreversible block copolymers containing reactive furfuryl groups via living anionic polymerization: the countercation effect on block copolymerization behavior

Journal Article · Fri Aug 07 00:00:00 EDT 2015 · Polymer Chemistry · OSTI ID:1523761

Kang, Beom-Goo; Pramanik, Nabendu B.; Singha, Nikhil K.; +2 more

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY