Transannularly conjugated tetrameric perylene diimide acceptors containing [2.2]paracyclophane for non-fullerene organic solar cells

Core engineering of perylene diimide (PDI)-based small molecular acceptors has played a critical role in boosting the device performances in the field of organic solar cells (OSCs). In this work, two regio-isomeric PDI-based acceptors (named oCP-FPDI4 and pCP-FPDI4) based on a novel [2.2]paracyclophane core were designed and synthesized. Due to the subtle variations in the functionalization positions on the [2.2]paracyclophane moiety, the two PDI acceptors exhibit different molecular geometries and absorption properties. When blended with a donor polymer named P3TEA, oCP-FPDI4 and pCP-FPDI4 showed dramatic differences in photovoltaic performances (2.42% vs. 9.06%). In-depth studies on the nano-scale morphology of the respective blend films revealed that the P3TEA:pCP-FPDI4 blend exhibited suitable phase segregation, thus contributing to better charge dissociation and less charge recombination. The marked variations in photovoltaic performances between oCP-FPDI4 and pCP-FPDI4 highlight the importance of regulating the spatial orientations in the design of PDI-based acceptors using cyclophane derivatives.

[1]  W. Ma,et al.  Perylene Diimide‐Based Nonfullerene Polymer Solar Cells with over 11% Efficiency Fabricated by Smart Molecular Design and Supramolecular Morphology Optimization , 2019, Advanced Functional Materials.

[2]  Zhaohui Wang,et al.  Rylene Annulated Subphthalocyanine: A Promising Cone-Shaped Non-Fullerene Acceptor for Organic Solar Cells , 2019, ACS Materials Letters.

[3]  B. Tang,et al.  Through-Space Conjugation: A Thriving Alternative for Optoelectronic Materials , 2019, CCS Chemistry.

[4]  H. Ade,et al.  Intramolecular π-stacked perylene-diimide acceptors for non-fullerene organic solar cells , 2019, Journal of Materials Chemistry A.

[5]  M. Mayor,et al.  Beyond Simple Substitution Patterns - Symmetrically Tetrasubstituted [2.2]Paracyclophanes as 3D Functional Materials , 2019, European Journal of Organic Chemistry.

[6]  Christoph J. Brabec,et al.  Critical review of the molecular design progress in non-fullerene electron acceptors towards commercially viable organic solar cells. , 2019, Chemical Society reviews.

[7]  Luping Yu,et al.  Conformational Flexibility Determines Electronic Coupling and Charge Transfer Character in Single Propeller-Shaped Perylene Diimide Tetramer Arrays , 2018, The Journal of Physical Chemistry C.

[8]  Yong Cao,et al.  Organic and solution-processed tandem solar cells with 17.3% efficiency , 2018, Science.

[9]  Yang Yang,et al.  Next-generation organic photovoltaics based on non-fullerene acceptors , 2018 .

[10]  Jianfei Wu,et al.  Iris-Like Acceptor with Most PDI Units for Organic Solar Cells. , 2018, ACS applied materials & interfaces.

[11]  H. Ade,et al.  Effect of Ring‐Fusion on Miscibility and Domain Purity: Key Factors Determining the Performance of PDI‐Based Nonfullerene Organic Solar Cells , 2018, Advanced Energy Materials.

[12]  He Yan,et al.  Material insights and challenges for non-fullerene organic solar cells based on small molecular acceptors , 2018, Nature Energy.

[13]  Jie Zhu,et al.  Over 14% Efficiency in Organic Solar Cells Enabled by Chlorinated Nonfullerene Small‐Molecule Acceptors , 2018, Advanced materials.

[14]  Fei Huang,et al.  Nonfullerene Acceptor Molecules for Bulk Heterojunction Organic Solar Cells. , 2018, Chemical reviews.

[15]  Seth R. Marder,et al.  Non-fullerene acceptors for organic solar cells , 2018 .

[16]  R. Friend,et al.  Organic solar cells based on non-fullerene acceptors. , 2018, Nature materials.

[17]  Feng Gao,et al.  Organic solar cells based on non-fullerene acceptors. , 2018, Nature materials.

[18]  H. Ade,et al.  Ring-Fusion of Perylene Diimide Acceptor Enabling Efficient Nonfullerene Organic Solar Cells with a Small Voltage Loss. , 2017, Journal of the American Chemical Society.

[19]  J. Xie,et al.  PDI Derivative through Fine-Tuning the Molecular Structure for Fullerene-Free Organic Solar Cells. , 2017, ACS applied materials & interfaces.

[20]  A. Hendsbee,et al.  Applying direct heteroarylation synthesis to evaluate organic dyes as the core component in PDI-based molecular materials for fullerene-free organic solar cells , 2017 .

[21]  Yun Zhang,et al.  Molecular Optimization Enables over 13% Efficiency in Organic Solar Cells. , 2017, Journal of the American Chemical Society.

[22]  Hongzheng Chen,et al.  Electron acceptors with varied linkages between perylene diimide and benzotrithiophene for efficient fullerene-free solar cells , 2017 .

[23]  Runnan Yu,et al.  Design, Synthesis, and Photovoltaic Characterization of a Small Molecular Acceptor with an Ultra-Narrow Band Gap. , 2017, Angewandte Chemie.

[24]  Fan Yang,et al.  An Electron Acceptor with Porphyrin and Perylene Bisimides for Efficient Non-Fullerene Solar Cells. , 2017, Angewandte Chemie.

[25]  M. Samoć,et al.  Fingerprints of Through-Bond and Through-Space Exciton and Charge π-Electron Delocalization in Linearly Extended [2.2]Paracyclophanes. , 2017, Journal of the American Chemical Society.

[26]  He Yan,et al.  Pronounced Effects of a Triazine Core on Photovoltaic Performance–Efficient Organic Solar Cells Enabled by a PDI Trimer‐Based Small Molecular Acceptor , 2017, Advanced materials.

[27]  N. Zhang,et al.  Propeller-Shaped Acceptors for High-Performance Non-Fullerene Solar Cells: Importance of the Rigidity of Molecular Geometry , 2017 .

[28]  Hongzheng Chen,et al.  A non-fullerene acceptor with a fully fused backbone for efficient polymer solar cells with a high open-circuit voltage , 2016 .

[29]  Xuhui Huang,et al.  Reduced Intramolecular Twisting Improves the Performance of 3D Molecular Acceptors in Non‐Fullerene Organic Solar Cells , 2016, Advanced materials.

[30]  M. Steigerwald,et al.  Electron Delocalization in Perylene Diimide Helicenes. , 2016, Angewandte Chemie.

[31]  N. Doltsinis,et al.  Three-Bladed Rylene Propellers with Three-Dimensional Network Assembly for Organic Electronics. , 2016, Journal of the American Chemical Society.

[32]  Luping Yu,et al.  Covalently Bound Clusters of Alpha-Substituted PDI-Rival Electron Acceptors to Fullerene for Organic Solar Cells. , 2016, Journal of the American Chemical Society.

[33]  M. Wasielewski,et al.  Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors. , 2016, Chemical science.

[34]  David Schmidt,et al.  Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials. , 2016, Chemical reviews.

[35]  Joshua H. Carpenter,et al.  Rigidifying Nonplanar Perylene Diimides by Ring Fusion Toward Geometry‐Tunable Acceptors for High‐Performance Fullerene‐Free Solar Cells , 2016, Advanced materials.

[36]  Xuhui Huang,et al.  The influence of spacer units on molecular properties and solar cell performance of non-fullerene acceptors , 2015 .

[37]  Matthew Y. Sfeir,et al.  Molecular helices as electron acceptors in high-performance bulk heterojunction solar cells , 2015, Nature Communications.

[38]  G. Bodwell,et al.  Cyclophanes containing large polycyclic aromatic hydrocarbons. , 2015, Chemical Society reviews.

[39]  A. Jen,et al.  A Tetraperylene Diimides Based 3D Nonfullerene Acceptor for Efficient Organic Photovoltaics , 2015, Advanced science.

[40]  Daoben Zhu,et al.  High-performance fullerene-free polymer solar cells with 6.31% efficiency , 2015 .

[41]  Xuhui Huang,et al.  A Tetraphenylethylene Core‐Based 3D Structure Small Molecular Acceptor Enabling Efficient Non‐Fullerene Organic Solar Cells , 2015, Advanced materials.

[42]  M. Steigerwald,et al.  Efficient organic solar cells with helical perylene diimide electron acceptors. , 2014, Journal of the American Chemical Society.

[43]  Tobin J Marks,et al.  Imide- and amide-functionalized polymer semiconductors. , 2014, Chemical reviews.

[44]  Daoben Zhu,et al.  A Star‐Shaped Perylene Diimide Electron Acceptor for High‐Performance Organic Solar Cells , 2014, Advanced materials.

[45]  T. Nakano,et al.  Energy-transfer properties of a [2.2]paracyclophane-based through-space dimer. , 2013, Chemistry.

[46]  Jian Pei,et al.  Towards rational design of organic electron acceptors for photovoltaics: a study based on perylenediimide derivatives , 2013 .

[47]  Long Ye,et al.  A Potential Perylene Diimide Dimer‐Based Acceptor Material for Highly Efficient Solution‐Processed Non‐Fullerene Organic Solar Cells with 4.03% Efficiency , 2013, Advanced materials.

[48]  J. Brédas,et al.  π-stacked oligo(phenylene vinylene)s based on pseudo-geminal substituted [2.2]paracyclophanes: impact of interchain geometry and interactions on the electronic properties. , 2012, Angewandte Chemie.

[49]  S. Sanvito,et al.  Efficient conducting channels formed by the π-π stacking in single [2,2]paracyclophane molecules. , 2012, The Journal of chemical physics.

[50]  Y. Chujo,et al.  Through-space conjugated polymers consisting of [2.2]paracyclophane , 2011 .

[51]  Mark A Ratner,et al.  Rylene and Related Diimides for Organic Electronics , 2011, Advanced materials.

[52]  T. Weil,et al.  The rylene colorant family--tailored nanoemitters for photonics research and applications. , 2010, Angewandte Chemie.

[53]  D. Collard,et al.  Multitiered 2D pi-stacked conjugated polymers based on pseudo-geminal disubstituted [2.2]paracyclophane. , 2010, Journal of the American Chemical Society.