Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells

Article

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
Article Title

Phthalimide and naphthalimide: Effect of end-capping groups on molecular properties and photovoltaic performance of 9-fluorenone based acceptors for organic solar cells

ERA Journal ID1012
Article CategoryArticle
AuthorsDo, Thu-Trang (Author), Subbiah, Jegadesan (Author), Manzhos, Sergei (Author), Jones, David J (Author), Bell, John M (Author) and Sonar, Prashant (Author)
Journal TitleOrganic Electronics
Journal Citation62, pp. 12-20
Number of Pages9
Year2018
Place of PublicationNetherlands
ISSN1566-1199
Digital Object Identifier (DOI)https://doi.org/10.1016/j.orgel.2018.06.040
Web Address (URL)https://www.sciencedirect.com/science/article/abs/pii/S1566119918303318?via%3Dihub
Abstract

A novel 2-butyloctyl (BO) substituted phthalimide (PI) end-capped fluorenone [PI-FN-PI (BO)] non-fullerene electron acceptor for organic photovoltaics has been designed and synthesized to study the effect of end-capping groups on the optoelectronic properties compared to our earlier reported naphthalimide (NAI) terminated fluorenone NAI-FN-NAI (BO) reference compound. The electron withdrawing terminal NAI groups were replaced by a PI group in order to evaluate the influence of electron affinity of such group on the lowest occupied molecular orbital (LUMO) energy level and other optoelectronic properties. The newly synthesized PI-FN-PI (BO) with a 2-butyloctyl alkyl chain is sparingly soluble in organic solvents due to its more planar structure and short alkyl chain. For organic solar cell devices, solubility of the active layer blend is extremely important so higher solubility is the key requirement. In order to enhance the solubility of the compound, we synthesized 2-decyltetradecyl (DT) substituted phthalimide (PI) end-capped fluorenone [PI-FN-PI (DT)]. Furthermore, another new compound NAI-FN-NAI (DT) was produced to compare with PI-FN-PI (DT) since both of these compounds have similar side alkyl chain and middle core but different end capping groups. It is clearly demonstrated that this simple chemical modification noticeably influences thermal, optical, electrochemical properties and significantly impacts the photovoltaic performance.

KeywordsPhthalimide; Naphthalimide; 9-Fluorenone; Non-fullerene; Electron acceptors; Organic solar cells
ANZSRC Field of Research 2020401699. Materials engineering not elsewhere classified
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Byline AffiliationsQueensland University of Technology
University of Melbourne
National University of Singapore
Institution of OriginUniversity of Southern Queensland
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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
Molecular engineering strategy for high efficiency fullerene-free organic solar cells using conjugated 1,8-naphthalimide and fluorenone building blocks
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
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
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