Deep Absorbing Porphyrin Small Molecule for High-Performance Organic Solar Cells with Very Low Energy Losses

Gao, Ke; Li, Lisheng; Lai, Tianqi; Xiao, Liangang; Huang, Yuan; Huang, Fei; Peng, Junbiao; Cao, Yong; Liu, Feng; Russell, Thomas P.; Janssen, René A.  J.; Peng, Xiaobin

doi:10.1021/jacs.5b03740

Deep Absorbing Porphyrin Small Molecule for High-Performance Organic Solar Cells with Very Low Energy Losses

Journal Article · Tue Jun 02 00:00:00 EDT 2015 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.5b03740· OSTI ID:1370256

Gao, Ke ^[1]; Li, Lisheng ^[1]; Lai, Tianqi ^[1]; Xiao, Liangang ^[1]; Huang, Yuan ^[1]; Huang, Fei ^[1]; Peng, Junbiao ^[1]; Cao, Yong ^[1]; Liu, Feng ^[2]; Russell, Thomas P. ^[3]; Janssen, René A. J. ^[4]; Peng, Xiaobin ^[1]

South China Univ. of Technology, Guangzhou (Poeple's Republic of China)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of Massachusetts, Amherst, MA (United States)
Eindhoven Univ. of Technology (The Netherlands)

In this work, we designed and synthesized the DPPEZnP-TEH molecule, with a porphyrin ring linked to two diketopyrrolopyrrole units by ethynylene bridges. The resulting material exhibits a very low energy band gap of 1.37 eV and a broad light absorption to 907 nm. An open-circuit voltage of 0.78 V was obtained in bulk heterojunction (BHJ) organic solar cells, showing a low energy loss of only 0.59 eV, which is the first report that small molecule solar cells show energy losses <0.6 eV. The optimized solar cells show remarkable external quantum efficiency, short circuit current, and power conversion efficiency up to 65%, 16.76 mA/cm², and 8.08%, respectively, which are the best values for BHJ solar cells with very low energy losses. Additionally, the morphology of DPPEZnP-TEH neat and blend films with PC61BM was studied thoroughly by grazing incidence X-ray diffraction, resonant soft X-ray scattering, and transmission electron microscopy under different fabrication conditions.

View Accepted Manuscript (DOE)

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Polymer-Based Materials for Harvesting Solar Energy (PHaSE); Univ. of Massachusetts, Amherst, MA (United States)

Sponsoring Organization:: International Science & Technology Cooperation Program of China; Ministry of Science and Technology of the People’s Republic of China (MOST); National Natural Science Foundation of China (NSFC); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0001087

OSTI ID:: 1370256

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 23 Vol. 137; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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A near-infrared non-fullerene electron acceptor for high performance polymer solar cells Li, Yongxi; Zhong, Lian; Gautam, Bhoj Energy & Environmental Science, Vol. 10, Issue 7 https://doi.org/10.1039/c7ee00844a	journal	January 2017
Simultaneous enhancement of the molecular planarity and the solubility of non-fullerene acceptors: effect of aliphatic side-chain substitution on the photovoltaic performance Zhang, Zhe; Li, Miao; Liu, Yahui Journal of Materials Chemistry A, Vol. 5, Issue 17 https://doi.org/10.1039/c7ta02141k	journal	January 2017
Side-chain engineering in a thermal precursor approach for efficient photocurrent generation Takahashi, Kohtaro; Kumagai, Daichi; Yamada, Naoya Journal of Materials Chemistry A, Vol. 5, Issue 27 https://doi.org/10.1039/c7ta04162d	journal	January 2017
Porphyrin based push–pull conjugates as donors for solution-processed bulk heterojunction solar cells: a case of metal-dependent power conversion efficiency Mishra, Ruchika; Regar, Ramprasad; Singhal, Rahul Journal of Materials Chemistry A, Vol. 5, Issue 30 https://doi.org/10.1039/c7ta05338j	journal	January 2017
Substituent effects in magnesium tetraethynylporphyrin with two diketopyrrolopyrrole units for bulk heterojunction organic solar cells Ogumi, Keisuke; Nakagawa, Takafumi; Okada, Hiroshi Journal of Materials Chemistry A, Vol. 5, Issue 44 https://doi.org/10.1039/c7ta07576f	journal	January 2017
Modulation of the power conversion efficiency of organic solar cells via architectural variation of a promising non-fullerene acceptor Mishra, Ruchika; Regar, Ramprasad; Singh, Varun Journal of Materials Chemistry A, Vol. 6, Issue 2 https://doi.org/10.1039/c7ta08533h	journal	January 2018
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Real-time tracing the changes in the intracellular pH value during apoptosis by near-infrared ratiometric fluorescence imaging Lin, Liyun; Zhao, Jingjin; Zhang, Liangliang Chemical Communications, Vol. 54, Issue 65 https://doi.org/10.1039/c8cc05385e	journal	January 2018
Singlet and triplet energy transfer dynamics in self-assembled axial porphyrin–anthracene complexes: towards supra-molecular structures for photon upconversion Gray, Victor; Küçüköz, Betül; Edhborg, Fredrik Physical Chemistry Chemical Physics, Vol. 20, Issue 11 https://doi.org/10.1039/c8cp00884a	journal	January 2018
Hole transporting materials for perovskite solar cells: a chemical approach Urieta-Mora, Javier; García-Benito, Inés; Molina-Ontoria, Agustín Chemical Society Reviews, Vol. 47, Issue 23 https://doi.org/10.1039/c8cs00262b	journal	January 2018
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Panchromatic ternary organic solar cells with 9.44% efficiency incorporating porphyrin-based donors Vartanian, Maida; de la Cruz, Pilar; Biswas, Subhayan Nanoscale, Vol. 10, Issue 25 https://doi.org/10.1039/c8nr02856g	journal	January 2018
BODIPY–diketopyrrolopyrrole–porphyrin conjugate small molecules for use in bulk heterojunction solar cells Bucher, Léo; Desbois, Nicolas; Koukaras, Emmanuel N. Journal of Materials Chemistry A, Vol. 6, Issue 18 https://doi.org/10.1039/c8ta01291a	journal	January 2018
A low-bandgap dimeric porphyrin molecule for 10% efficiency solar cells with small photon energy loss Xiao, Liangang; Lai, Tianqi; Liu, Xiang Journal of Materials Chemistry A, Vol. 6, Issue 38 https://doi.org/10.1039/c8ta05903a	journal	January 2018
Recent progress in porphyrin-based materials for organic solar cells Mahmood, Asif; Hu, Jian-Yong; Xiao, Bo Journal of Materials Chemistry A, Vol. 6, Issue 35 https://doi.org/10.1039/c8ta06392c	journal	January 2018
Star-shaped magnesium tetraethynylporphyrin bearing four peripheral electron-accepting diketopyrrolopyrrole functionalities for organic solar cells Wang, Huan; Yue, Qihui; Nakagawa, Takafumi Journal of Materials Chemistry A, Vol. 7, Issue 8 https://doi.org/10.1039/c8ta10710f	journal	January 2019
Terminal group engineering for small-molecule donors boosts the performance of nonfullerene organic solar cells Duan, Tainan; Tang, Hua; Liang, Ru-Ze Journal of Materials Chemistry A, Vol. 7, Issue 6 https://doi.org/10.1039/c8ta11420j	journal	January 2019
Design of asymmetric benzodithiophene based wide band-gap conjugated polymers toward efficient polymer solar cells promoted by a low boiling point additive Li, Yonghai; Duan, Linrui; Liu, Deyu Journal of Materials Chemistry C, Vol. 6, Issue 11 https://doi.org/10.1039/c8tc00148k	journal	January 2018
Enhanced light-harvesting of benzodithiophene conjugated porphyrin electron donors in organic solar cells Zhou, Xuan; Tang, Wei; Bi, Pengqing Journal of Materials Chemistry C, Vol. 7, Issue 2 https://doi.org/10.1039/c8tc04495c	journal	January 2019
An all-small-molecule organic solar cell derived from naphthalimide for solution-processed high-efficiency nonfullerene acceptors Yadagiri, B.; Narayanaswamy, K.; Revoju, Srikanth Journal of Materials Chemistry C, Vol. 7, Issue 3 https://doi.org/10.1039/c8tc05692g	journal	January 2019
Study of perovskite solar cells based on mixed-organic-cation FA _x MA _1−x PbI ₃ absorption layer Yang, Yufeng; Luo, Jundong; Wei, Aixiang Physical Chemistry Chemical Physics, Vol. 21, Issue 22 https://doi.org/10.1039/c9cp02003a	journal	January 2019
Design of single-porphyrin donors toward high open-circuit voltage for organic solar cells via an energy level gradient-distribution screening strategy of fragments: a theoretical study Wu, Li-Na; Sui, Ming-Yue; Xiao, Song Physical Chemistry Chemical Physics, Vol. 22, Issue 7 https://doi.org/10.1039/c9cp04903g	journal	January 2020
Phthalocyanines and porphyrinoid analogues as hole- and electron-transporting materials for perovskite solar cells Urbani, Maxence; de la Torre, Gema; Nazeeruddin, Mohammad Khaja Chemical Society Reviews, Vol. 48, Issue 10 https://doi.org/10.1039/c9cs00059c	journal	January 2019
Effect of linear side-chain length on the photovoltaic performance of benzodithiophene- alt -dicarboxylic ester terthiophene polymers Ma, Kangqiao; Zhang, Tao; Wan, Pan New Journal of Chemistry, Vol. 43, Issue 33 https://doi.org/10.1039/c9nj02484k	journal	January 2019
Branched versus linear: side-chain effect on fluorinated wide bandgap donors and their applications in organic solar cells Duan, Tainan; Liang, Ru-Ze; Fu, Yingying New Journal of Chemistry, Vol. 44, Issue 3 https://doi.org/10.1039/c9nj04621f	journal	January 2020
Semitransparent solar cells with over 12% efficiency based on a new low bandgap fluorinated small molecule acceptor Luo, Mei; Zhao, Chunyan; Yuan, Jun Materials Chemistry Frontiers, Vol. 3, Issue 11 https://doi.org/10.1039/c9qm00499h	journal	January 2019
Efficient as-cast thick film small-molecule organic solar cell with less fluorination on the donor Wang, Kai; Song, Xin; Guo, Xiao Materials Chemistry Frontiers, Vol. 4, Issue 1 https://doi.org/10.1039/c9qm00605b	journal	January 2020
High-yielding Pd ₂ (dba) ₃ ·C ₆ H ₆ -based four-fold Sonogashira coupling with selenophene-conjugated magnesium tetraethynylporphyrin for organic solar cells Wang, Huan; Nakagawa, Takafumi; Zhang, Meng-Meng RSC Advances, Vol. 9, Issue 56 https://doi.org/10.1039/c9ra07393k	journal	January 2019
An environmentally friendly natural polymer as a universal interfacial modifier for fullerene and non-fullerene polymer solar cells Wang, Xiaojing; Yi, Shuwang; He, Zhicai Sustainable Energy & Fuels, Vol. 4, Issue 3 https://doi.org/10.1039/c9se01079c	journal	January 2020
Diketopyrrolopyrrole-based conjugated materials for non-fullerene organic solar cells Zhao, Chaowei; Guo, Yiting; Zhang, Yuefeng Journal of Materials Chemistry A, Vol. 7, Issue 17 https://doi.org/10.1039/c9ta01976f	journal	January 2019
Impact of end groups on the performance of non-fullerene acceptors for organic solar cell applications Suman, Suman; Singh, Surya Prakash Journal of Materials Chemistry A, Vol. 7, Issue 40 https://doi.org/10.1039/c9ta08620j	journal	January 2019
Cathode interlayer-free organic solar cells with enhanced device performance upon alcohol treatment Chen, Xuebin; Zhu, Bei; Kan, Bin Journal of Materials Chemistry C, Vol. 7, Issue 26 https://doi.org/10.1039/c9tc01039d	journal	January 2019
Improving the efficiencies of small molecule solar cells by solvent vapor annealing to enhance J-aggregation Xiao, Liangang; Li, Zhengdong; Hu, Qin Journal of Materials Chemistry C, Vol. 7, Issue 31 https://doi.org/10.1039/c9tc02630d	journal	January 2019
A bacteriochlorin-diketopyrrolopyrrole triad as a donor for solution-processed bulk heterojunction organic solar cells Ponsot, Flavien; Bucher, Léo; Desbois, Nicolas Journal of Materials Chemistry C, Vol. 7, Issue 31 https://doi.org/10.1039/c9tc02724f	journal	January 2019
Self-doping n-type polymer as a cathode interface layer enables efficient organic solar cells by increasing built-in electric field and boosting interface contact Wang, Yufei; Liang, Zezhou; Li, Xiaoming Journal of Materials Chemistry C, Vol. 7, Issue 36 https://doi.org/10.1039/c9tc03506k	journal	January 2019
Rational molecular design towards NIR absorption: efficient diketopyrrolopyrrole derivatives for organic solar cells and photothermal therapy Patil, Yuvraj; Misra, Rajneesh Journal of Materials Chemistry C, Vol. 7, Issue 42 https://doi.org/10.1039/c9tc03640g	journal	January 2019
Bis(benzothiophene- S , S -dioxide) fused small molecules realize solution-processible, high-performance and non-doped blue organic light-emitting diodes Hu, Liwen; Liu, Siyang; Xie, Guohua Journal of Materials Chemistry C, Vol. 8, Issue 3 https://doi.org/10.1039/c9tc05019a	journal	January 2020
Non-fullerene organic solar cells based on a BODIPY-polymer as electron donor with high photocurrent Liu, Baiqiao; Ma, Zaifei; Xu, Yunhua Journal of Materials Chemistry C, Vol. 8, Issue 7 https://doi.org/10.1039/c9tc05480d	journal	January 2020
Non-toxic green food additive enables efficient polymer solar cells through adjusting the phase composition distribution and boosting charge transport Li, Jianfeng; Wang, Yufei; Liang, Zezhou Journal of Materials Chemistry C, Vol. 8, Issue 7 https://doi.org/10.1039/c9tc06571g	journal	January 2020
Organic solar cells: Materials and prospects of graphene for active and interfacial layers Amollo, Tabitha A.; Mola, Genene T.; Nyamori, Vincent O. Critical Reviews in Solid State and Materials Sciences, Vol. 45, Issue 4 https://doi.org/10.1080/10408436.2019.1632791	journal	June 2019
Two dimensional self-assembly zinc porphyrin and zinc phthalocyanine heterojunctions with record high power conversion efficiencies Yu, Junting; Jiang, Zhou; Hao, Yifan Journal of Physics: Condensed Matter, Vol. 30, Issue 25 https://doi.org/10.1088/1361-648x/aac502	journal	June 2018
Novel dithienopyrrole-based molecular donor materials for organic solar cells Zhang, Zong-Bing; Xu, Jia-Wei; Zhang, Xin-Yu Functional Materials Letters, Vol. 10, Issue 06 https://doi.org/10.1142/s1793604717500850	journal	December 2017
Synthesis and Photovoltaic Effect of Electron-Withdrawing Units for Low Band Gap Conjugated Polymers Bearing Bi(thienylenevinylene) Side Chains Li, Jianfeng; Wang, Yufei; Wang, Ningning Polymers, Vol. 11, Issue 9 https://doi.org/10.3390/polym11091461	journal	September 2019

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