Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks

Article

Do, Thu Trang, Pham, Hong Duc, Manzhos, Sergei, Bell, John M and Sonar, Prashant. 2017. "Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks." ACS Applied Materials and Interfaces. 9 (20), pp. 16967-16976. https://doi.org/10.1021/acsami.6b16395
Article Title

Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks

ERA Journal ID40638
Article CategoryArticle
AuthorsDo, Thu Trang (Author), Pham, Hong Duc (Author), Manzhos, Sergei (Author), Bell, John M (Author) and Sonar, Prashant (Author)
Journal TitleACS Applied Materials and Interfaces
Journal Citation9 (20), pp. 16967-16976
Number of Pages10
Year2017
PublisherAmerican Chemical Society
Place of PublicationUnited States
ISSN1944-8244
1944-8252
Digital Object Identifier (DOI)https://doi.org/10.1021/acsami.6b16395
Web Address (URL)https://pubs.acs.org/doi/10.1021/acsami.6b16395
Abstract

We designed, synthesized, and characterized a series of novel electron deficient small molecule nonfullerene acceptors based on 1,8-naphthalimide (NAI) and 9-fluorenone (FN) with different branched alkyl chains using various techniques. These molecules are based on an acceptor-donor-acceptor-donor-acceptor (A1-D-A2-D-A1) molecular design configuration with NAI as the end-capping acceptor (A1), FN as electron-withdrawing central (A2) group, and thiophene ring as a donor (D) unit. These materials are named as NAI-FN-NAI (BO) and NAI-FN-NAI (HD) where BO and HD represent butyloctyl and hexyldecyl alkyl groups, respectively. To further modify energy levels of these materials, we converted the weak electron withdrawing ketonic group (C=O) attached to the FN moiety of NAI-FN-NAI (BO) to a stronger electron withdrawing cyano group (C≡N) to obtain the compound NAI-FCN-NAI (BO) by keeping the same alkyl chain. The optical, electrochemical, and thermal properties of the new acceptors were studied. The materials exhibited higher to medium band gaps, low lowest unoccupied molecular orbital (LUMO) energy levels, and highly thermally stable properties. Organic solar cell devices employing conventional poly(3-hexylthiophene) (P3HT) a donor polymer and the newly designed small molecules as the acceptor were investigated. Among all new materials, organic solar cell devices based on NAI-FN-NAI (BO) as an acceptor exhibit the highest performance with an open circuit voltage (VOC) of 0.88 V, a short-circuit current density (JSC) of 9.1 mAcm-2, a fill factor (FF) of 45%, and an overall power conversion efficiency (PCE) of 3.6%. This is the first report of 9-fluorenone based nonfullerene acceptor with P3HT donor in organic solar cell devices with such a promising performance.

Keywords1.8-naphthalimide; 9-fluorenone; nonfullerene; electron acceptors; organic solar cells
ANZSRC Field of Research 2020401699. Materials engineering not elsewhere classified
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Byline AffiliationsQueensland University of Technology
National University of Singapore
Open access urlhttps://pubs.acs.org/doi/10.1021/acsami.6b16395
Institution of OriginUniversity of Southern Queensland
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Liu, Qian, Wang, Yang, Kohara, Akihiro, Matsumoto, Hidetoshi, Manzhos, Sergei, Feron, Krishna, Bottle, Steven E., Bell, John, Michinobu, Tsuyoshi and Sonar, Prashant. 2020. "Tuning the charge carrier polarity of organic transistors by varying the electron affinity of the flanked units in diketopyrrolopyrrole-based copolymers." Advanced Functional Materials. 30 (7). https://doi.org/10.1002/adfm.201907452
Naphthalene flanked diketopyrrolopyrrole: A new DPP family member and its comparative optoelectronic properties with thiophene- and furan- flanked DPP counterparts
Liu, Qian, Sun, Huabin, Ponnappa, Supreetha Paleyanda, Feron, Krishna, Manzhos, Sergei, Jones, Michael W.M., Bottle, Steven E., Bell, John, Noh, Yong-Young and Sonar, Prashant. 2019. "Naphthalene flanked diketopyrrolopyrrole: A new DPP family member and its comparative optoelectronic properties with thiophene- and furan- flanked DPP counterparts." Organic Electronics. 74, pp. 290-298. https://doi.org/10.1016/j.orgel.2019.07.017
Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors
Liu, Qian, Sun, Huabin, Blaikie, Chula, Caporale, Chiara, Manzhos, Sergei, Feron, Krishna, MacLeod, Jennifer M., Massi, Massimiliano, Bottle, Steven E., Bell, John, Noh, Yong-Young and Sonar, Prashant. 2018. "Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors." New Journal of Chemistry: a journal for new directions in chemistry. 42 (15), pp. 12374-12385. https://doi.org/10.1039/c8nj01453a
High density mechanical energy storage with carbon nanothread bundle
Zhan, Haifei, Zhang, Gang, Bell, John M., Tan, Vincent B. C. and Gu, Yuantong. 2020. "High density mechanical energy storage with carbon nanothread bundle." Nature Communications. 11 (1). https://doi.org/10.1038/s41467-020-15807-7
Synergistic use of pyridine and selenophene in a diketopyrrolopyrrole-based conjugated polymer enhances the electron mobility in organic transistors
Liu, Qian, Kumagai, Shohei, Manzhos, Sergei, Chen, Yingqian, Angunawela, Indunil, Nahid, Masrur Morshed, Feron, Krishna, Bottle, Steven E, Bell, John, Ade, Harald, Takeya, Jun and Sonar, Prashant. 2020. "Synergistic use of pyridine and selenophene in a diketopyrrolopyrrole-based conjugated polymer enhances the electron mobility in organic transistors." Advanced Functional Materials. 34 (1). https://doi.org/10.1002/adfm.202000489
Oriented graphenes from plasma-reformed coconut oil for supercapacitor electrodes
Kumar, Shailesh, Martin, Phil, Bendavid, Avi, Bell, John and Ostrikov, Kostya (Ken). 2019. "Oriented graphenes from plasma-reformed coconut oil for supercapacitor electrodes." Nanomaterials. 9 (12). https://doi.org/10.3390/nano9121679
Predicting single-layer technetium dichalcogenides (TcX2, X = S, Se) with promising applications in photovoltaics and photocatalysis
Jiao, Yalong, Zhou, Liujiang, Ma, Fengxian, Gao, Guoping, Kou, Liangzhi, Bell, John, Sanvito, Stefano and Du, Aijun. 2016. "Predicting single-layer technetium dichalcogenides (TcX2, X = S, Se) with promising applications in photovoltaics and photocatalysis." ACS Applied Materials and Interfaces. 8 (8), pp. 5385-5392. https://doi.org/10.1021/acsami.5b12606
Ab initio study of two-dimensional PdPS as an ideal light harvester and promising catalyst for hydrogen evolution reaction
Jiao, Yalong, Ma, Fengxian, Zhou, Liujiang, Ng, Yun Hau, Bell, John, Tretiak, Sergei and Du, Aijun. 2018. "Ab initio study of two-dimensional PdPS as an ideal light harvester and promising catalyst for hydrogen evolution reaction." Materials Today Energy. 7, pp. 136-140. https://doi.org/10.1016/j.mtener.2018.01.005
Strain mediated bandgap reduction, light spectrum broadening, and carrier mobility enhancement of methylammonium lead/tin iodide perovskites
Jiao, Yalong, Ma, Fengxian, Wang, Hongxia, Bell, John and Du, Aijun. 2017. "Strain mediated bandgap reduction, light spectrum broadening, and carrier mobility enhancement of methylammonium lead/tin iodide perovskites." Particle and Particle Systems Characterization. 34 (4). https://doi.org/10.1002/ppsc.201600288
Two-dimensional boron hydride sheets: High stability, massless dirac fermions, and excellent mechanical properties
Jiao, Yalong, Ma, Fengxian, Bell, John, Bilic, Ante and Du, Aijun. 2016. "Two-dimensional boron hydride sheets: High stability, massless dirac fermions, and excellent mechanical properties." Angewandte Chemie. 55 (35), pp. 10292-10295. https://doi.org/10.1002/anie.201604369
Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells
Do, Thu-Trang, Subbiah, Jegadesan, Manzhos, Sergei, Jones, David J, Bell, John M and Sonar, Prashant. 2018. "Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells." Organic Electronics. 62, pp. 12-20. https://doi.org/10.1016/j.orgel.2018.06.040
Vinylene and benzo[c] [1,2,5]thiadiazole: Effect of the pi-spacer unit on the properties of bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing polymers for n-channel organic field-effect transistors
Do, Thu Trang, Patil, Basanagouda B, Singh, Samarendra P, Yambem, Soniya D, Feron, Krishna, Ostrikov, Kostya (Ken), Bell, John M and Sonar, Prashant. 2018. "Vinylene and benzo[c] [1,2,5]thiadiazole: Effect of the pi-spacer unit on the properties of bis(2-oxoindolin-3-ylidene)-benzodifuran-dione containing polymers for n-channel organic field-effect transistors." RSC Advances: an international journal to further the chemical sciences. 8 (68), pp. 38919-38928. https://doi.org/10.1039/c8ra08890j
Indenofluorene-based-copolymers: Influence of electron-deficient benzothiadiazole (BT) and benzooxadiazole (BO) moieties on light emitting devices
Do, Thu-Trang, Matsuki, Keiichiro, Sakanoue, Tomo, Wong, Fu-Lung, Manzhos, Sergei, Lee, Chun-Sing, Bell, John, Takenobu, Taishi and Sonar, Prashant. 2019. "Indenofluorene-based-copolymers: Influence of electron-deficient benzothiadiazole (BT) and benzooxadiazole (BO) moieties on light emitting devices." Organic Electronics. 70, pp. 14-24. https://doi.org/10.1016/j.orgel.2019.03.050
Microstructure and mechanical properties of titanium/steel bimetallic joints
Chu, Qiaoling, Bai, Ruixiang, Zhang, Min, Li, Jihong, Lei, Zhenkun, Hu, Ning, Bell, John M and Yan, Cheng. 2017. "Microstructure and mechanical properties of titanium/steel bimetallic joints." Materials Characterization. 132, pp. 330-337. https://doi.org/10.1016/j.matchar.2017.08.025
Correction: Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors (New Journal of Chemistry (2018) 42 (12374–12385) DOI: 10.1039/C8NJ01453A)
Liu, Qian, Sun, Huabin, Blaikie, Chula, Caporale, Chiara, Manzhos, Sergei, Feron, Krishna, MacLeod, Jennifer M., Massi, Massimiliano, Bottle, Steven E., Bell, John, Noh, Yong-Young and Sonar, Prashant. 2018. "Correction: Naphthalene flanked diketopyrrolopyrrole based organic semiconductors for high performance organic field effect transistors (New Journal of Chemistry (2018) 42 (12374–12385) DOI: 10.1039/C8NJ01453A)." New Journal of Chemistry: a journal for new directions in chemistry. 42 (19), p. 16384. https://doi.org/10.1039/C8NJ90083C
Benefit assessment of battery plus solar for customers and the grid
Boulaire, Fanny, Narimani, Afsaneh, Bell, John, Drogemuller, Robin, Vine, Desley, Buys, Laurie and Walker, Geoffrey. 2019. "Benefit assessment of battery plus solar for customers and the grid." Energy Strategy Reviews. 26. https://doi.org/10.1016/j.esr.2019.100372
Atypical defect motions in brittle layered sodium titanate nanowires
Bo, Arixin, Chen, Kai, Pickering, Edmund, Zhan, Haifei, Bell, John, Du, Aijun, Zhang, Yongqiang, Wang, Xiaoguang, Zhu, Huaiyong, Shan, Zhiwei and Gu, Yuantong. 2018. "Atypical defect motions in brittle layered sodium titanate nanowires." Journal of Physical Chemistry Letters. 9 (20), pp. 6052-6059. https://doi.org/10.1021/acs.jpclett.8b02349
Building energy optimisation under uncertainty using ACOMV algorithm
Bamdad, Keivan, Cholette, Michael E, Guan, Lisa and Bell, John. 2018. "Building energy optimisation under uncertainty using ACOMV algorithm." Energy and Buildings. 167, pp. 322-333. https://doi.org/10.1016/j.enbuild.2018.02.053
Ant colony algorithm for building energy optimisation problems and comparison with benchmark algorithms
Bamdad, Keivan, Cholette, Michael E, Guan, Lisa and Bell, John. 2017. "Ant colony algorithm for building energy optimisation problems and comparison with benchmark algorithms." Energy and Buildings. 154, pp. 404-414. https://doi.org/10.1016/j.enbuild.2017.08.071
Low hysteresis perovskite solar cells using an electron-beam evaporated WO3-x thin film as the electron transport layer
Ali, Fawad, Pham, Ngoc Duy, Fan, Lijuan, Tiong, Vincent, Ostrikov, Ken, Bell, John M., Wang, Hongxia and Tesfamichael, Tuquabo. 2019. "Low hysteresis perovskite solar cells using an electron-beam evaporated WO3-x thin film as the electron transport layer." ACS Applied Energy Materials. 2 (8), pp. 5456-5464. https://doi.org/10.1021/acsaem.9b00547
Tuning the amount of oxygen vacancies in sputter-deposited SnOx films for enhancing the performance of perovskite solar cells
Ali, Fawad, Pham, Ngoc Duy, Bradford, H. Jonathan, Khoshsirat, Nima, Ostrikov, Ken, Bell, John M, Wang, Hongxia and Tesfamichael, Tuquabo. 2018. "Tuning the amount of oxygen vacancies in sputter-deposited SnOx films for enhancing the performance of perovskite solar cells." ChemSusChem: chemistry and sustainability, energy and materials. 11 (18), pp. 3096-3103. https://doi.org/10.1002/cssc.201801541
Stretchable respiration sensors: Advanced designs and multifunctional platforms for wearable physiological monitoring
Dinh, Toan, Nguyen, Thanh, Phan, Hoang-Phuong, Nguyen, Nam-Trung, Dao, Dzung Viet and Bell, John. 2020. "Stretchable respiration sensors: Advanced designs and multifunctional platforms for wearable physiological monitoring." Biosensors and Bioelectronics. 166. https://doi.org/10.1016/j.bios.2020.112460
True Meaning of Pseudocapacitors and Their Performance Metrics: Asymmetric versus Hybrid Supercapacitors
Chodankar, Nilesh R., Pham, Hong Duc, Nanjundan, Ashok Kumar, Fernando, Joseph F. S., Jayaramulu, Kolleboyina, Golberg, Dmitri, Han, Young-Kyu and Dubal, Deepak P.. 2020. "True Meaning of Pseudocapacitors and Their Performance Metrics: Asymmetric versus Hybrid Supercapacitors." Small. 16 (37). https://doi.org/10.1002/smll.202002806
Investigation on Temperature-Dependent Electrical Conductivity of Carbon Nanotube/Epoxy Composites for Sustainable Energy Applications
Njuguna, Michael K., Galpaya, Dilini, Yan, Cheng, Colwell, Colwell, Will, Geoffrey, Hu, Ning, Yarlagadda, Prasad and Bell, John M.. 2015. "Investigation on Temperature-Dependent Electrical Conductivity of Carbon Nanotube/Epoxy Composites for Sustainable Energy Applications." Journal of Nanoscience and Nanotechnology. 15 (9), pp. 6957-6964. https://doi.org/10.1166/jnn.2015.10514
Ethanol sensitivity of thermally evaporated nanostructured WO3 thin films doped and implanted with Fe
Ahsan, M., Ahmad, M. Z., Tesfamichael, T., Bell, J. and Yarlagadda, Prasad K. D. V.. 2013. "Ethanol sensitivity of thermally evaporated nanostructured WO3 thin films doped and implanted with Fe." 2nd International Conference on Measurement, Instrumentation and Automation (ICMIA 2013). China 23 - 24 Apr 2013 Scientific.Net. https://doi.org/10.4028/www.scientific.net/AMM.333-335.1938