Conjugated ladder polymers by a cyclopentannulation polymerization

Bheemireddy, Sambasiva R.; Hautzinger, Matthew P.; Li, Tao; Lee, Byeongdu; Plunkett, Kyle N.

doi:10.1021/jacs.6b12916

Title: Conjugated ladder polymers by a cyclopentannulation polymerization

Journal Article · Mon Apr 03 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.6b12916· OSTI ID:1364137

Bheemireddy, Sambasiva R. ^[1]; Hautzinger, Matthew P. ^[1]; Li, Tao ^[2];

^[2];

^[1]

Southern Illinois Univ., Carbondale, IL (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)

Here, we report a nontraditional synthesis of cyclopentafused-polycyclic aromatic hydrocarbon embedded ladder polymers using a palladium catalyzed cyclopentannulation polymerization followed by a cyclodehydrogenation reaction. Donor–acceptor type polymers containing a cyclopenta[hi]aceanthrylene acceptor groups can be synthesized by a palladium catalyzed copolymerization between 9,10-dibromoanthracene and a variety of bis(arylethynyl)arenes to give polymers with molecular weights (Mn) of 9–22 kDa. The bis(arylethynyl)arenes were composed of benzene, thiophene, or thieno[3,2-b]thiophene moieties, which provided access to a series of four donor–acceptor copolymers. The polymers were subjected to cyclodehydrogenation with FeCl₃ to access rigid ladder type polymers with the conversion investigated by ¹³C NMR of isotopically labeled polymers. As a result, the ladder polymers possess broad UV–Vis absorptions and narrow optical band gaps of 1.17–1.29 eV and are p-type semiconductors in organic field effect transistors.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Scientific User Facilities Division; National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1364137

Journal Information:: Journal of the American Chemical Society, Vol. 139, Issue 16; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 77 works

Citation information provided by
Web of Science

References (60)

Recent Advances in Bulk Heterojunction Polymer Solar Cells Lu, Luyao; Zheng, Tianyue; Wu, Qinghe Chemical Reviews, Vol. 115, Issue 23 https://doi.org/10.1021/acs.chemrev.5b00098	journal	August 2015
Conjugated Polymer-Based Organic Solar Cells Günes, Serap; Neugebauer, Helmut; Sariciftci, Niyazi Serdar Chemical Reviews, Vol. 107, Issue 4, p. 1324-1338 https://doi.org/10.1021/cr050149z	journal	April 2007
Ladder Oligo( p -phenylenevinylene)s with Silicon and Carbon Bridges Xu, Caihong; Wakamiya, Atsushi; Yamaguchi, Shigehiro Journal of the American Chemical Society, Vol. 127, Issue 6 https://doi.org/10.1021/ja042964m	journal	February 2005
Ladder Polymers: The new generation Schlüter, Arnulf-Dieter Advanced Materials, Vol. 3, Issue 6 https://doi.org/10.1002/adma.19910030603	journal	June 1991
Synthesis of a fully unsaturated all-carbon ladder polymer Schlüter, A. -D.; Löffler, M.; Enkelmann, V. Nature, Vol. 368, Issue 6474 https://doi.org/10.1038/368831a0	journal	April 1994
Polyarylenes and poly(arylenevinylene)s: 8. The first soluble ladder polymer with 1,4-benzoquinone-bismethide subunits Scherf, Ullrich; Müllen, Klaus Polymer, Vol. 33, Issue 11 https://doi.org/10.1016/0032-3861(92)90543-6	journal	January 1992
Band-Shaped Structures by Repetitive Cycloaddition Reactions of Benzo[1,2-b:4,5-b′]bisthiete Meier, Herbert; Rose, Bernd; Schollmeyer, Dieter Liebigs Annalen, Vol. 1997, Issue 6 https://doi.org/10.1002/jlac.199719970619	journal	June 1997
Directed Electrophilic Cyclizations: Efficient Methodology for the Synthesis of Fused Polycyclic Aromatics Goldfinger, Marc B.; Crawford, Khushrav B.; Swager, Timothy M. Journal of the American Chemical Society, Vol. 119, Issue 20 https://doi.org/10.1021/ja9642673	journal	May 1997
Thermodynamic synthesis of solution processable ladder polymers Lee, Jongbok; Rajeeva, Bharath Bangalore; Yuan, Tianyu Chemical Science, Vol. 7, Issue 2 https://doi.org/10.1039/C5SC02385H	journal	January 2016
Self-Assembly, Molecular Packing, and Electron Transport in n-Type Polymer Semiconductor Nanobelts Briseno, Alejandro L.; Mannsfeld, Stefan C. B.; Shamberger, Patrick J. Chemistry of Materials, Vol. 20, Issue 14 https://doi.org/10.1021/cm8010265	journal	July 2008
Room-temperature Bose–Einstein condensation of cavity exciton–polaritons in a polymer Plumhof, Johannes D.; Stöferle, Thilo; Mai, Lijian Nature Materials, Vol. 13, Issue 3 https://doi.org/10.1038/nmat3825	journal	December 2013
Two-Dimensional Graphene Nanoribbons Yang, Xiaoyin; Dou, Xi; Rouhanipour, Ali Journal of the American Chemical Society, Vol. 130, Issue 13 https://doi.org/10.1021/ja710234t	journal	April 2008
Ladder-type materials Scherf, Ullrich Journal of Materials Chemistry, Vol. 9, Issue 9 https://doi.org/10.1039/a900447e	journal	January 1999
New Conjugated Ladder Polymer Containing Carbazole Moieties Patil, S. A.; Scherf, U.; Kadashchuk, A. Advanced Functional Materials, Vol. 13, Issue 8 https://doi.org/10.1002/adfm.200304344	journal	August 2003
Synthesis of a Novel Poly(iptycene) Ladder Polymer Chen, Zhihua; Amara, John P.; Thomas, Samuel W. Macromolecules, Vol. 39, Issue 9 https://doi.org/10.1021/ma052451f	journal	May 2006
Synthesis of planar poly( p -phenylene) derivatives for maximization of extended π-conjugation Tour, James M.; Lamba, Jaydeep J. S. Macromolecular Symposia, Vol. 77, Issue 1 https://doi.org/10.1002/masy.19940770140	journal	January 1994
A simple two‐step synthesis of a novel, fully aromatic ladder‐type polymer Chmil, Knut; Scherf, Ullrich Die Makromolekulare Chemie, Rapid Communications, Vol. 14, Issue 4, p. 217-222 https://doi.org/10.1002/marc.1993.030140401	journal	April 1993
Fused Polycyclic Aromatics via Electrophile-Induced Cyclization Reactions: Application to the Synthesis of Graphite Ribbons Goldfinger, Marc B.; Swager, Timothy M. Journal of the American Chemical Society, Vol. 116, Issue 17 https://doi.org/10.1021/ja00096a056	journal	August 1994
Bottom-Up Synthesis of Soluble and Narrow Graphene Nanoribbons Using Alkyne Benzannulations Yang, Wenlong; Lucotti, Andrea; Tommasini, Matteo Journal of the American Chemical Society, Vol. 138, Issue 29 https://doi.org/10.1021/jacs.6b03014	journal	July 2016
Ambipolar Transport in Solution-Synthesized Graphene Nanoribbons Gao, Jia; Uribe-Romo, Fernando J.; Saathoff, Jonathan D. ACS Nano, Vol. 10, Issue 4 https://doi.org/10.1021/acsnano.6b00643	journal	April 2016
Polyaromatic Ribbons from Oligo-Alkynes via Selective Radical Cascade: Stitching Aromatic Rings with Polyacetylene Bridges Byers, Philip M.; Alabugin, Igor V. Journal of the American Chemical Society, Vol. 134, Issue 23 https://doi.org/10.1021/ja3023626	journal	May 2012
One-shot K-region-selective annulative π-extension for nanographene synthesis and functionalization Ozaki, Kyohei; Kawasumi, Katsuaki; Shibata, Mari Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms7251	journal	February 2015
Oligomers and Polymers Based on Bridged Phenylenes as Electronic Materials Grimsdale, Andrew C.; Müllen, Klaus Macromolecular Rapid Communications, Vol. 28, Issue 17 https://doi.org/10.1002/marc.200700247	journal	September 2007
High Electron Mobility in Ladder Polymer Field-Effect Transistors Babel, Amit; Jenekhe, Samson A. Journal of the American Chemical Society, Vol. 125, Issue 45, p. 13656-13657 https://doi.org/10.1021/ja0371810	journal	November 2003
Direct Light-Driven Water Oxidation by a Ladder-Type Conjugated Polymer Photoanode Bornoz, Pauline; Prévot, Mathieu S.; Yu, Xiaoyun Journal of the American Chemical Society, Vol. 137, Issue 49 https://doi.org/10.1021/jacs.5b05724	journal	December 2015
Ladder-type conjugated oligomers prepared by the Scholl oxidative cyclodehydrogenation reaction: synthesis, characterization and application in field effect transistors Huang, Wei; Zhang, Hejian; Ma, Ji Journal of Materials Chemistry C, Vol. 3, Issue 24 https://doi.org/10.1039/C5TC00354G	journal	January 2015
High Intrachain Hole Mobility on Molecular Wires of Ladder-Type Poly( $p$ -Phenylenes) Prins, P.; Grozema, F. C.; Schins, J. M. Physical Review Letters, Vol. 96, Issue 14 https://doi.org/10.1103/PhysRevLett.96.146601	journal	April 2006
Fully Conjugated Porphyrin Tapes with Electronic Absorption Bands That Reach into Infrared Tsuda, A. Science, Vol. 293, Issue 5527 https://doi.org/10.1126/science.1059552	journal	July 2001
Big Is Beautiful−“Aromaticity” Revisited from the Viewpoint of Macromolecular and Supramolecular Benzene Chemistry Watson, Mark D.; Fechtenkötter, Andreas; Müllen, Klaus Chemical Reviews, Vol. 101, Issue 5 https://doi.org/10.1021/cr990322p	journal	May 2001
Linear Monodisperse π-Conjugated Oligomers: Model Compounds for Polymers and More Martin, Rainer E.; Diederich, François Angewandte Chemie International Edition, Vol. 38, Issue 10 https://doi.org/10.1002/(SICI)1521-3773(19990517)38:10<1350::AID-ANIE1350>3.0.CO;2-6	journal	May 1999
Carbon-bridged oligo(p-phenylenevinylene)s for photostable and broadly tunable, solution-processable thin film organic lasers Morales-Vidal, Marta; Boj, Pedro G.; Villalvilla, José M. Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms9458	journal	September 2015
Donor–acceptor conjugated polymers based on multifused ladder-type arenes for organic solar cells Wu, Jhong-Sian; Cheng, Sheng-Wen; Cheng, Yen-Ju Chemical Society Reviews, Vol. 44, Issue 5 https://doi.org/10.1039/C4CS00250D	journal	January 2015
Synthesis and Characterization of Solution-Processable Ladderized n-Type Naphthalene Bisimide Copolymers for OFET Applications Durban, Matthew M.; Kazarinoff, Peter D.; Segawa, Yukari Macromolecules, Vol. 44, Issue 12 https://doi.org/10.1021/ma2004822	journal	June 2011
Contorted aromatics via a palladium-catalyzed cyclopentannulation strategy Bheemireddy, Sambasiva R.; Ubaldo, Pamela C.; Finke, Aaron D. Journal of Materials Chemistry C, Vol. 4, Issue 18 https://doi.org/10.1039/C5TC02305J	journal	January 2016
Cross-coupling reactions for preparation of π-conjugated polymers Yamamoto, Takakazu Journal of Organometallic Chemistry, Vol. 653, Issue 1-2 https://doi.org/10.1016/S0022-328X(02)01261-5	journal	July 2002
Synthesis of conjugated oligomers and polymers: the organometallic way Babudri, Francesco; Farinola, Gianluca M.; Naso, Francesco Journal of Materials Chemistry, Vol. 14, Issue 1 https://doi.org/10.1039/b309515k	journal	January 2004
New synthetic method for the polymerization of alkylthiophenes Se´vignon, Marc; Papillon, Julien; Schulz, Emmanuelle Tetrahedron Letters, Vol. 40, Issue 32 https://doi.org/10.1016/S0040-4039(99)01164-8	journal	August 1999
Palladium-catalyzed synthesis of oligo(alkylthiophenes) Hassan, Jwanro; Schulz, Emmanuelle; Gozzi, Christel Journal of Molecular Catalysis A: Chemical, Vol. 195, Issue 1-2 https://doi.org/10.1016/S1381-1169(02)00543-5	journal	March 2003
Palladium-Catalyzed Dehydrohalogenative Polycondensation of 2-Bromo-3-hexylthiophene: An Efficient Approach to Head-to-Tail Poly(3-hexylthiophene) Wang, Qifeng; Takita, Ryo; Kikuzaki, Yuuta Journal of the American Chemical Society, Vol. 132, Issue 33 https://doi.org/10.1021/ja105767z	journal	August 2010
Semiconducting Polymers Prepared by Direct Arylation Polycondensation Facchetti, Antonio; Vaccaro, Luigi; Marrocchi, Assunta Angewandte Chemie International Edition, Vol. 51, Issue 15 https://doi.org/10.1002/anie.201200199	journal	March 2012
C–H Arylation Reaction: Atom Efficient and Greener Syntheses of π-Conjugated Small Molecules and Macromolecules for Organic Electronic Materials Okamoto, Ken; Zhang, Junxiang; Housekeeper, Jeremy B. Macromolecules, Vol. 46, Issue 20 https://doi.org/10.1021/ma401190r	journal	August 2013
Efficient Synthesis of Rigid Ladder Polymers via Palladium Catalyzed Annulation Liu, Sheng; Jin, Zexin; Teo, Yew Chin Journal of the American Chemical Society, Vol. 136, Issue 50 https://doi.org/10.1021/ja5110415	journal	December 2014
Multicomponent Polycoupling of Internal Diynes, Aryl Diiodides, and Boronic Acids to Functional Poly(tetraarylethene)s Liu, Yajing; Roose, Jesse; Lam, Jacky W. Y. Macromolecules, Vol. 48, Issue 22 https://doi.org/10.1021/acs.macromol.5b01946	journal	October 2015
Aggregation-Induced Emission and Photocyclization of Poly(hexaphenyl-1,3-butadiene)s Synthesized from “1 + 2” Polycoupling of Internal Alkynes and Arylboronic Acids Liu, Yajing; Lam, Jacky W. Y.; Zheng, Xiaoyan Macromolecules, Vol. 49, Issue 16 https://doi.org/10.1021/acs.macromol.6b01148	journal	August 2016
Polyarylcyanation of Diyne: A One-Pot Three-Component Convenient Route for In Situ Generation of Polymers with AIE Characteristics Qiu, Zijie; Han, Ting; Kwok, Ryan T. K. Macromolecules, Vol. 49, Issue 23 https://doi.org/10.1021/acs.macromol.6b02098	journal	November 2016
Palladium catalysed cascade cycloaddition reactions. General concepts and illustrative examples. Grigg, Ronald; Kennewell, Peter; Teasdale, Andrew Tetrahedron Letters, Vol. 34, Issue 1 https://doi.org/10.1016/S0040-4039(00)60081-3	journal	January 1993
Palladium-Catalyzed Formation of Aceanthrylenes: A Simple Method for Peri-Cyclopentenelation of Aromatic Compounds Dang, Hung; Garcia-Garibay, Miguel A. Journal of the American Chemical Society, Vol. 123, Issue 2 https://doi.org/10.1021/ja002329q	journal	December 2000
One Step Pd(0)-Catalyzed Synthesis, X-ray Analysis, and Photophysical Properties of Cyclopent[ hi ]aceanthrylene: Fullerene-like Properties in a Nonalternant Cyclopentafused Aromatic Hydrocarbon Dang, Hung; Levitus, Marcia; Garcia-Garibay, Miguel A. Journal of the American Chemical Society, Vol. 124, Issue 1 https://doi.org/10.1021/ja016189b	journal	January 2002
Palladium-Catalyzed Pentannulation of Polycyclic Aromatic Hydrocarbons Lütke Eversloh, Christian; Avlasevich, Yuri; Li, Chen Chemistry - A European Journal, Vol. 17, Issue 45 https://doi.org/10.1002/chem.201101126	journal	September 2011
Palladium-Catalyzed Annulation of 9-Halophenanthrenes with Alkynes: Synthesis, Structural Analysis, and Properties of Acephenanthrylene-Based Derivatives Liu, En-Chih; Chen, Min-Kuan; Li, Jen-Yi Chemistry - A European Journal, Vol. 21, Issue 12 https://doi.org/10.1002/chem.201405763	journal	February 2015
Stabilizing Pentacene By Cyclopentannulation Bheemireddy, Sambasiva R.; Ubaldo, Pamela C.; Rose, Peter W. Angewandte Chemie International Edition, Vol. 54, Issue 52 https://doi.org/10.1002/anie.201508650	journal	November 2015
Dicyclopenta[cd,jk]pyrene based acceptors in conjugated polymers Bheemireddy, Sambasiva R.; Plunkett, Kyle N. Polymer Chemistry, Vol. 7, Issue 2 https://doi.org/10.1039/C5PY01582K	journal	January 2016
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
Controlling the Scholl Reaction King, Benjamin T.; Kroulík, Jiří; Robertson, Charles R. The Journal of Organic Chemistry, Vol. 72, Issue 7 https://doi.org/10.1021/jo061515x	journal	March 2007
A universal calibration for gel permeation chromatography Grubisic, Z.; Rempp, P.; Benoit, H. Journal of Polymer Science Part B: Polymer Letters, Vol. 5, Issue 9 https://doi.org/10.1002/pol.1967.110050903	journal	September 1967
Alternate donor-acceptor small-band-gap semiconducting polymers; Polysquaraines and polycroconaines Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Synthetic Metals, Vol. 55, Issue 1 https://doi.org/10.1016/0379-6779(93)90949-W	journal	March 1993
Electron Acceptors Based on Functionalizable Cyclopenta[ hi ]aceanthrylenes and Dicyclopenta[ de,mn ]tetracenes Wood, Jordan D.; Jellison, Jessica L.; Finke, Aaron D. Journal of the American Chemical Society, Vol. 134, Issue 38 https://doi.org/10.1021/ja304602t	journal	September 2012
Orthogonal Functionalization of Cyclopenta[ hi ]aceanthrylenes Lee, Che-Hsiung; Plunkett, Kyle N. Organic Letters, Vol. 15, Issue 6 https://doi.org/10.1021/ol400093g	journal	March 2013
Redox properties of non-alternant cyclopenta-fused polycyclic aromatic hydrocarbons: The effect of peripheral pentagon annelation Koper, Carola; Sarobe, Martin; Jenneskens, Leonardus W. Phys. Chem. Chem. Phys., Vol. 6, Issue 2 https://doi.org/10.1039/B312234D	journal	January 2004
Benzotrithiophene-Based Donor–Acceptor Copolymers with Distinct Supramolecular Organizations Guo, Xin; Puniredd, Sreenivasa Reddy; Baumgarten, Martin Journal of the American Chemical Society, Vol. 134, Issue 20 https://doi.org/10.1021/ja302957s	journal	May 2012

Cited By (21)

Polycyclic Aromatic Hydrocarbons as Potential Building Blocks for Organic Solar Cells Aumaitre, Cyril; Morin, Jean‐François The Chemical Record, Vol. 19, Issue 6 https://doi.org/10.1002/tcr.201900016	journal	February 2019
Diels–Alder polymerization: a versatile synthetic method toward functional polyphenylenes, ladder polymers and graphene nanoribbons Hou, Ian Cheng-Yi; Hu, Yunbin; Narita, Akimitsu Polymer Journal, Vol. 50, Issue 1 https://doi.org/10.1038/pj.2017.69	journal	November 2017
β-Strand inspired bifacial π-conjugated polymers Chaudhuri, Saikat; Mohanan, Manikandan; Willems, Andreas V. Chemical Science, Vol. 10, Issue 23 https://doi.org/10.1039/c9sc01724k	journal	January 2019
Dicyclohepta[ ijkl , uvwx ]rubicene with Two Pentagons and Two Heptagons as a Stable and Planar Non‐benzenoid Nanographene Zhang, Xi‐Sha; Huang, Yan‐Ying; Zhang, Jing Angewandte Chemie, Vol. 132, Issue 9 https://doi.org/10.1002/ange.201914416	journal	January 2020
Layered Thiadiazoloquinoxaline-Containing Long Pyrene-Fused N-Heteroacenes Hu, Ben-Lin; Zhang, Ke; An, Cunbin Angewandte Chemie, Vol. 130, Issue 38 https://doi.org/10.1002/ange.201803230	journal	August 2018
Towards Nonalternant Nanographenes through Self‐Promoted Intramolecular Indenoannulation Cascade by C−F Bond Activation Akhmetov, Vladimir; Feofanov, Mikhail; Papaianina, Olena Chemistry – A European Journal, Vol. 25, Issue 50 https://doi.org/10.1002/chem.201903467	journal	August 2019
Cyclopentannulation and cyclodehydrogenation of isomerically pure 5,11-dibromo-anthradithiophenes leading to contorted aromatics Bheemireddy, Sambasiva R.; Hussain, Waseem A.; Uddin, Ain Chemical Communications, Vol. 54, Issue 100 https://doi.org/10.1039/c8cc07327a	journal	January 2018
Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes Gadakh, Sunita; Shimon, Linda J. W.; Gidron, Ori Angewandte Chemie International Edition, Vol. 56, Issue 44 https://doi.org/10.1002/anie.201705914	journal	October 2017
Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures Jolly, Anthony; Miao, Dandan; Daigle, Maxime Angewandte Chemie, Vol. 132, Issue 12 https://doi.org/10.1002/ange.201906379	journal	December 2019
Quadrupolar Cyclopenta[ hi ]aceanthrylene‐Based Electron Donor‐Acceptor‐Donor Conjugates: Charge Transfer versus Charge Separation Schierl, Christoph; Alex, Wiebke; Mateo, Luis M. Angewandte Chemie, Vol. 131, Issue 41 https://doi.org/10.1002/ange.201906206	journal	September 2019
Emerging Bottom‐Up Strategies for the Synthesis of Graphene Nanoribbons and Related Structures Jolly, Anthony; Miao, Dandan; Daigle, Maxime Angewandte Chemie International Edition, Vol. 59, Issue 12 https://doi.org/10.1002/anie.201906379	journal	December 2019
Synthesis and properties of five ring fused aromatic compounds based on S , S -dioxide benzothiophene Zhang, Yuhao; Peng, Feng; He, Ruifeng New Journal of Chemistry, Vol. 42, Issue 4 https://doi.org/10.1039/c7nj04306f	journal	January 2018
Quadrupolar Cyclopenta[ hi ]aceanthrylene-Based Electron Donor-Acceptor-Donor Conjugates: Charge Transfer versus Charge Separation Schierl, Christoph; Alex, Wiebke; Mateo, Luis M. Angewandte Chemie International Edition, Vol. 58, Issue 41 https://doi.org/10.1002/anie.201906206	journal	September 2019
Dimesitylboryl‐Decorated Azaarene: Synthesis, Enhanced Stability and Optoelectronic Property Jin, Pengcheng; Tian, Feng; Han, Yanbing Chemistry – An Asian Journal, Vol. 14, Issue 23 https://doi.org/10.1002/asia.201901349	journal	October 2019
Layered Thiadiazoloquinoxaline-Containing Long Pyrene-Fused N-Heteroacenes Hu, Ben-Lin; Zhang, Ke; An, Cunbin Angewandte Chemie International Edition, Vol. 57, Issue 38 https://doi.org/10.1002/anie.201803230	journal	August 2018
Dicyclohepta[ ijkl , uvwx ]rubicene with Two Pentagons and Two Heptagons as a Stable and Planar Non‐benzenoid Nanographene Zhang, Xi‐Sha; Huang, Yan‐Ying; Zhang, Jing Angewandte Chemie International Edition, Vol. 59, Issue 9 https://doi.org/10.1002/anie.201914416	journal	January 2020
Cyclopentannulation and Cyclodehydrogenation of Isomerically Pure 5,11-Dibromo-Anthradithiophenes Leading to Contorted Aromatics Bheemireddy, Sambasiva; Hussain, Waseem A.; Uddin, Ain https://doi.org/10.26434/chemrxiv.7066622	posted_content	September 2018
Regioselective Transformation of Long π-Conjugated Backbones: From Oligofurans to Oligoarenes Gadakh, Sunita; Shimon, Linda J. W.; Gidron, Ori Angewandte Chemie, Vol. 129, Issue 44 https://doi.org/10.1002/ange.201705914	journal	October 2017
Towards Nonalternant Nanographenes through Self‐Promoted Intramolecular Indenoannulation Cascade by C−F Bond Activation Akhmetov, Vladimir; Feofanov, Mikhail; Papaianina, Olena Chemistry – A European Journal, Vol. 25, Issue 50 https://doi.org/10.1002/chem.201902586	journal	August 2019
Cyclopentannulation and Cyclodehydrogenation of Isomerically Pure 5,11-Dibromo-Anthradithiophenes Leading to Contorted Aromatics Bheemireddy, Sambasiva; Hussain, Waseem A.; Uddin, Ain https://doi.org/10.26434/chemrxiv.7066622.v1	posted_content	September 2018
Synthesis and Characterization of Fully Conjugated Ladder Naphthalene Bisimide Copolymers Liu, Feng; Wu, Yonggang; Wang, Chao Polymers, Vol. 10, Issue 7 https://doi.org/10.3390/polym10070790	journal	July 2018

Similar Records

Molecular Interactions and Ordering in Electrically Doped Polymers: Blends of PBTTT and F4TCNQ

Journal Article · Fri Sep 12 00:00:00 EDT 2014 · Macromolecules · OSTI ID:1364137

Cochran, Justin E; Junk, Matthias J. N.; Glaudell, Anne M.; +6 more

All-Polymer Solar Cell Performance Optimized via Systematic Molecular Weight Tuning of Both Donor and Acceptor Polymers

Journal Article · Thu Dec 31 00:00:00 EST 2015 · Journal of the American Chemical Society · OSTI ID:1364137

Zhou, Nanjia; Dudnik, Alexander S.; Li, Ting I. N. G.; +10 more