Design and synthesis of new ultra-low band gap thiadiazoloquinoxaline-based polymers for near-infrared organic photovoltaic application

Кештов, М. Л.; Kuklin, S. A.; Radychev, N. A.; Nikolaev, A. Yu.; Koukaras, Emmanuel Ν.; Sharma, Abhishek; Sharma, Ganesh D.

doi:10.1039/c5ra24364e

Cited by 26 publications

(19 citation statements)

References 80 publications

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“…In addition, Hu et al reported low‐bandgap polymers based on the building block 7‐perfluorophenyl‐6 H ‐[1,2,5]thiadiazole[3,4‐g]benzoimidazole, which yielded a PCE of 1.92% . To enhance the electron‐accepting strength of thiadiazoloquinoxaline (TDQ), Keshtov et al introduced fluorene and thiazole substitutes into TDQ to yield F2 . The corresponding copolymer features an ultralow bandgap of 1.08 eV.…”

Section: Nir Photoelectric Materials For Opvsmentioning

confidence: 99%

Near‐infrared organic photoelectric materials for light‐harvesting systems: Organic photovoltaics and organic photodiodes

Xie

Chen

Ying

et al. 2019

InfoMat

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The inherent advantages of organic optoelectronic materials endow lightharvesting systems, including organic photovoltaics (OPVs) and organic photodiodes (OPDs), with multiple advantages, such as low-cost manufacturing, light weight, flexibility, and applicability to large-area fabrication, make them promising competitors with their inorganic counterparts. Among them, nearinfrared (NIR) organic optoelectronic materials occupy a special position and have become the subject of extensive research in both academia and industry.The introduction of NIR materials into OPVs extends the absorption spectrum range, thereby enhancing the photon-harvesting ability of the devices, due to which they have been widely used for the construction of semitransparent solar cells with single-junction or tandem architectures. NIR photodiodes have tremendous potential in industrial, military, and scientific applications, such as remote control of smart electronic devices, chemical/biological sensing, environmental monitoring, optical communication, and so forth. These practical and potential applications have stimulated the development of NIR photoelectric materials, which in turn has given impetus to innovation in light-harvesting systems. In this review, we summarize the common molecular design strategies of NIR photoelectric materials and enumerate their applications in OPVs and OPDs. K E Y W O R D Snear infrared, organic optoelectronic materials, organic photodiodes, organic photovoltaics

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Section: Nir Photoelectric Materials For Opvsmentioning

confidence: 99%

Near‐infrared organic photoelectric materials for light‐harvesting systems: Organic photovoltaics and organic photodiodes

Xie

Chen

Ying

et al. 2019

InfoMat

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“…In addition, the TQ-based polymers can also be applied to electrochromic devices 62 and polymer solar cells 63 . For example, Andersson and his coworkers reported two electrochromic polymers based on the TQ unit (P1 and P2, Fig.…”

Section: Pdimentioning

confidence: 99%

Benzothiadiazole and its π-extended, heteroannulated derivatives: useful acceptor building blocks for high-performance donor–acceptor polymers in organic electronics

2016

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The past five years have witnessed significant achievements in the field of flexible, stretchable, and printable organic electronics, especially polymer-based organic photovoltaics (OPVs) and organic fieldeffect transistors (OFETs), which have become competitive to their inorganic counterparts. One of the main driving forces attributed to this remarkable progress is the rapid development of semiconducting 10 polymeric materials. Therefore, the design and synthesis of new building blocks for efficient polymer semiconductors has attracted increasing attention from both the academic and industrial communities. This review attempts to critically summarize the recent advances with respect to the electron-deficient building blocks based on benzothiadiazole and its π-extended, heteroannulated derivatives, which have been mostly developed over the past five years for constructing π-conjugated polymers, particularly 15 donor-acceptor (D-A) polymers. Semiconducting polymers containing these building blocks have demonstrated interesting properties and promising performances as active layers in OPVs and OFETs. The structural implications related to the performances of organic electronic devices are discussed. R SN SeN SeS TQ fDTBT CBT APhTQ BDTTQ BTI DTPBT DTNT TNTPT triple fused ring structures tetracyclic structures other large extended benzothiadiazole derivatives heteroatom substituted benzothiadiazolederivatives Chart 1 The chemical structures of benzothiadiazole and its π-extended, heteroannulated derivatives.Journal Name, [year], [vol], 00-00 | 13 eV. On the other hand, deep E LUMO levels can be obtained in BBT-based polymers, as represented by the E LUMO of −4.20 eV for PBBTPD (Chart 3). The difference between the E HOMO and E LUMO levels, called an electrochemical band gap, has a correlation with the end absorption of the UV-vis-NIR spectrum. 5 Notes and references 30The electron-deficient building blocks based on benzothiadiazole and its π-extended, heteroannulated derivatives for constructing high-performance semiconducting polymers are described.

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“…The results reported in the present work are in the range reported in the literature as was shown previously. The optical band gap of P3HTA and P3HTB were calculated from UV–vis absorption onset using the Equation as reported by Patra et al and Keshtov et al

B a n d g a p = \frac{1240}{λ_{o n s e t}}

…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Characterization of Poly(3‐Hexylthiophene) for Organic Solar Cells

Santos

Arias

Marques

et al. 2019

Macromolecular Symposia

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Poly(3‐hexylthiophene) (P3HT) has been successfully synthesized through McCullough route. The influence of nickel catalyst content on molar mass (Mn and Mw), dispersity (Đ), regioregularity (rr), as well as optical, thermal, and morphological properties is systematically investigated. The results evidence that polymer dispersities are narrow, Mn and rr values decrease with the augmentation of catalyst content. Polymer solution in different solvents (chloroform and dichlorobenzene) show similar optical band gaps. Solid state band gap of obtained material is lower than in solution, which confirms the reorganization of polymer chains in solid state. Both polymers show good thermal stability and their morphologies are tightly influenced by the monomer/catalyst ratio in the synthesis. Two main morphologies are obtained, for the higher molar mass P3HT it is nodule‐like, while the lower Mn presented rod form. The fore polymer combined with PCMB results in lower root mean square (RMS) indicating smoother morphology, which is more appropriate for solar cells application.

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Design and synthesis of new ultra-low band gap thiadiazoloquinoxaline-based polymers for near-infrared organic photovoltaic application

Abstract: Two D–A copolymers, F1 and F2, with fluorene and thiazole units were substituted, respectively, on a thiadiazoloquinoxaline (TDQ) unit to enhance the electron-accepting strength of TDQ.

Cited by 26 publications

References 80 publications

Near‐infrared organic photoelectric materials for light‐harvesting systems: Organic photovoltaics and organic photodiodes

Near‐infrared organic photoelectric materials for light‐harvesting systems: Organic photovoltaics and organic photodiodes

Benzothiadiazole and its π-extended, heteroannulated derivatives: useful acceptor building blocks for high-performance donor–acceptor polymers in organic electronics

Synthesis and Characterization of Poly(3‐Hexylthiophene) for Organic Solar Cells

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