Improved Photovoltaic Properties of Donor–Acceptor Copolymers by Introducing Quinoxalino[2,3-b′]porphyrin as a Light-Harvesting Unit

Donor–acceptor (D–A) copolymerization is an effective approach to construct low bandgap polymers with tunable electronic energy levels for the application as donor materials in polymer solar cells (PSCs). Usually, D–A copolymers possess an intramolecular charge transfer absorption band at long wavelength direction, so that the absorption of the polymers is broadened. However, absorption at short wavelength direction is also important and should be broadened and enhanced to increase the short-circuit current density (Jsc) of the PSCs. In this study, a series of low bandgap conjugated polymers, P(QP4-BT-DPP1), P(QP1-BT-DPP1), and P(QP1-BT-DPP4), based on two acceptor units quinoxalino[2,3-b′]porphyrin (QP) and diketopyrrolopyrrole (DPP) connected by oligothiophene donor units, were designed and synthesized by palladium-catalyzed Stille-coupling polymerization. As a complementary light-harvesting unit, QP was first introduced into the D–A conjugated polymers for improving the photovoltaic performance of PSCs...

[1]  Chain‐Shu Hsu,et al.  Porphyrin‐Incorporated 2D D–A Polymers with Over 8.5% Polymer Solar Cell Efficiency , 2014, Advanced materials.

[2]  Xuedong Wang,et al.  Diketopyrrolopyrrole–Thiophene–Benzothiadiazole Random Copolymers: An Effective Strategy To Adjust Thin-Film Crystallinity for Transistor and Photovoltaic Properties , 2013 .

[3]  T. Russell,et al.  Semi-crystalline random conjugated copolymers with panchromatic absorption for highly efficient polymer solar cells , 2013 .

[4]  Yang Yang,et al.  A Selenium‐Substituted Low‐Bandgap Polymer with Versatile Photovoltaic Applications , 2013, Advanced materials.

[5]  Yang Yang,et al.  A polymer tandem solar cell with 10.6% power conversion efficiency , 2013, Nature Communications.

[6]  Yongfang Li,et al.  Effect of Oligothiophene π-Bridge Length on the Photovoltaic Properties of D–A Copolymers Based on Carbazole and Quinoxalinoporphyrin , 2012 .

[7]  F. Huang,et al.  Recent development of push–pull conjugated polymers for bulk-heterojunction photovoltaics: rational design and fine tailoring of molecular structures , 2012 .

[8]  Yang Yang,et al.  Dual Plasmonic Nanostructures for High Performance Inverted Organic Solar Cells , 2012, Advanced materials.

[9]  Yang Yang,et al.  Tandem polymer solar cells featuring a spectrally matched low-bandgap polymer , 2012, Nature Photonics.

[10]  Yongfang Li,et al.  Effects of π-Conjugated Bridges on Photovoltaic Properties of Donor-π-Acceptor Conjugated Copolymers , 2012 .

[11]  Yongfang Li Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption. , 2012, Accounts of chemical research.

[12]  W. You,et al.  Rational Design of High Performance Conjugated Polymers for Organic Solar Cells , 2012 .

[13]  John R. Reynolds,et al.  High-efficiency inverted dithienogermole–thienopyrrolodione-based polymer solar cells , 2011, Nature Photonics.

[14]  Yong Cao,et al.  Simultaneous Enhancement of Open‐Circuit Voltage, Short‐Circuit Current Density, and Fill Factor in Polymer Solar Cells , 2011, Advanced materials.

[15]  C. Kan,et al.  Tuning the donor-acceptor strength of low-bandgap platinum-acetylide polymers for near-infrared photovoltaic applications. , 2011, Macromolecular rapid communications.

[16]  U. Jeng,et al.  Improving Device Efficiency of Polymer/Fullerene Bulk Heterojunction Solar Cells Through Enhanced Crystallinity and Reduced Grain Boundaries Induced by Solvent Additives , 2011, Advanced materials.

[17]  A. Heeger,et al.  A Porphyrin–Fullerene Dyad with a Supramolecular “Double‐Cable” Structure as a Novel Electron Acceptor for Bulk Heterojunction Polymer Solar Cells , 2011, Advanced materials.

[18]  Song Chen,et al.  Dithienogermole as a fused electron donor in bulk heterojunction solar cells. , 2011, Journal of the American Chemical Society.

[19]  Wai Kin Chan,et al.  Synthesis and Photovoltaic Properties of New Metalloporphyrin-Containing Polyplatinyne Polymers , 2011 .

[20]  Wei You,et al.  Development of fluorinated benzothiadiazole as a structural unit for a polymer solar cell of 7 % efficiency. , 2011, Angewandte Chemie.

[21]  Wei You,et al.  Fluorine substituted conjugated polymer of medium band gap yields 7% efficiency in polymer-fullerene solar cells. , 2011, Journal of the American Chemical Society.

[22]  S. Beaupré,et al.  Bulk heterojunction solar cells using thieno[3,4-c]pyrrole-4,6-dione and dithieno[3,2-b:2',3'-d]silole copolymer with a power conversion efficiency of 7.3%. , 2011, Journal of the American Chemical Society.

[23]  H. Sirringhaus,et al.  Thieno[3,2-b]thiophene-diketopyrrolopyrrole-containing polymers for high-performance organic field-effect transistors and organic photovoltaic devices. , 2011, Journal of the American Chemical Society.

[24]  Deborah K. Schneiderman,et al.  Oligothiophene Tetracyanobutadienes: Alternative Donor−Acceptor Architectures for Molecular and Polymeric Materials† , 2011 .

[25]  Wai-Yeung Wong,et al.  Organometallic photovoltaics: a new and versatile approach for harvesting solar energy using conjugated polymetallaynes. , 2010, Accounts of chemical research.

[26]  Lei Yan,et al.  Very-low-bandgap metallopolyynes of platinum with a cyclopentadithiophenone ring for organic solar cells absorbing down to the near-infrared spectral region. , 2010, Macromolecular rapid communications.

[27]  Wei You,et al.  A weak donor-strong acceptor strategy to design ideal polymers for organic solar cells. , 2010, ACS applied materials & interfaces.

[28]  Wai-Yeung Wong,et al.  Recent Progress on the Photonic Properties of Conjugated Organometallic Polymers Built Upon the trans-Bis(para-ethynylbenzene)bis(phosphine)platinum(II) Chromophore and Related Derivatives. , 2010, Macromolecular rapid communications.

[29]  Bin Zhao,et al.  Synthesis and photovoltaic properties of polythiophene stars with porphyrin core , 2010 .

[30]  Yong Cao,et al.  Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. , 2009, Accounts of chemical research.

[31]  Osamu Yoshikawa,et al.  Synthesis and Photophysical and Photovoltaic Properties of Porphyrin−Furan and −Thiophene Alternating Copolymers , 2009 .

[32]  Yongfang Li,et al.  Conjugated Polymer Photovoltaic Materials with Broad Absorption Band and High Charge Carrier Mobility , 2008 .

[33]  Wai-Yeung Wong,et al.  Metallated conjugated polymers as a new avenue towards high-efficiency polymer solar cells. , 2007, Nature materials.

[34]  K. Ohkubo,et al.  Porphyrin-diones and porphyrin-tetraones: reversible redox units being localized within the porphyrin macrocycle and their effect on tautomerism. , 2007, Journal of the American Chemical Society.

[35]  Zhan'ao Tan,et al.  Synthesis and photovoltaic properties of two-dimensional conjugated polythiophenes with bi(thienylenevinylene) side chains. , 2006, Journal of the American Chemical Society.

[36]  Christoph J. Brabec,et al.  Design Rules for Donors in Bulk‐Heterojunction Solar Cells—Towards 10 % Energy‐Conversion Efficiency , 2006 .

[37]  T. Balaban Tailoring porphyrins and chlorins for self-assembly in biomimetic artificial antenna systems. , 2005, Accounts of chemical research.

[38]  Yongfang Li,et al.  Synthesis and electroluminescence of novel copolymers containing crown ether spacers , 2003 .

[39]  J. Fréchet,et al.  Polymer-fullerene composite solar cells. , 2008, Angewandte Chemie.