Synthesis and Properties of Dithiafulvenyl Functionalized Spiro[fluorene-9,9′-xanthene] Molecules

Wu, Min; Li, Juan; Zhang, Ruqin; Xia, Tian; Han, Zhaoxiang; Lu, Xiaoqing; Guo, Kunpeng; Liu, Zhike; Wang, Zhongqiang

doi:10.1021/acs.orglett.7b03918

Cited by 30 publications

(14 citation statements)

References 40 publications

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“…The introduction of sulfur in the linker groups is another feasible strategy. Overall, thioether bonds, [ 171 ] thiophene, [ 172 ] dithiafulvenyl, [ 173 ] and PTZ [ 174 ] are feasible choices for introducing sulfur into the linker. Chen et al compared the different linkers OMeTAD and p ‐methylsulfanyl triphenylamine (SMeTAD).…”

Section: Chalcogen Compound Htmsmentioning

confidence: 99%

Recent Progress in Perovskite Solar Cells Modified by Sulfur Compounds

et al. 2021

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In the past decade, organic–inorganic hybrid perovskite solar cells (PSCs) have begun to be increasingly studied worldwide owing to the superior properties of perovskite material. However, some issues have delayed their commercialization, such as their long‐term stability, cost reduction, scale‐up ability, and efficiency. The introduction of sulfur to PSCs can relieve the above issues because sulfur can passivate interfacial trap states, suppress charge recombination, and inhibit ion migration, thereby enhancing the stability of PSCs. Furthermore, PbS bonds provide new channels for carrier extraction. Herein, the sulfur‐based compounds utilized in PSCs are summarized and classified according to their functions in the different layers of PSCs. The results indicate that these sulfur‐based compounds have efficiently promoted the commercialization of PSCs. It is hoped that this review can help others understand the intrinsic phenomena of sulfur‐based PSCs and motivate additional investigations.

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Section: Chalcogen Compound Htmsmentioning

confidence: 99%

Recent Progress in Perovskite Solar Cells Modified by Sulfur Compounds

et al. 2021

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“…The valence band (VB) edge ( E v ), onset ( E v – E F ) and secondary electron cut off ( E cut‐off ) energy regions in the UPS spectra are shown in Figure a. In the case of UPS, HOMO levels were obtained using the equation HOMO = 21.22– E Cut‐off + ( E V – E F ), while it was associated with the first oxidation potential ( E ox ) in CV (Figure b) . It was found the HOMO level of 2 m F‐X59 from the UPS analysis and CV measurement showed good consistency, both giving a −5.14 eV value (Table ).…”

Section: Resultsmentioning

confidence: 99%

“…However, such dopants are sensitive to moisture, leading to decomposition of the perovskite materials and instability of PSCs . In this context, great research interests have focused on the development of sensitive‐dopant‐free HTMs in PSCs …”

Section: Introductionmentioning

confidence: 99%

Introduction of Fluorine Into spiro[fluorene‐9,9′‐xanthene]‐Based Hole Transport Material to Obtain Sensitive‐Dopant‐Free, High Efficient and Stable Perovskite Solar Cells

Guo

Yang

et al. 2019

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Despite the substantial development of efficient hole transporting materials (HTMs) for high‐performance perovskite solar cells (PSCs), optimization of the HTMs to sensitive‐dopant‐free HTMs for high efficient PSCs with prominent stability have rarely been reported. Herein, a low‐cost fluorinated spiro[fluorene‐9,9′‐xanthene] based HTM termed 2mF‐X59 is designed and synthesized. In comparison with its reported nonfluorinated counterpart X59, 2mF‐X59 shows lowered highest occupied molecular orbital (HOMO) level, improved hole mobility, and hydrophobicity. Aided by 2,3,5,6‐tetrafluoro‐7,7,8,8‐tetracyanoquinodimethane (F4TCNQ) to further lower the HOMO level of 2mF‐X59 and improve its hole transfer, the optimized 2mF‐X59 based PSCs show a maximum power conversion efficiency (PCE) of 18.13% without the use of any sensitive‐dopants (e.g., lithium salt/4‐tert‐butylpyridine), which is comparable to the Spiro‐OMeTAD based PSCs (18.22%) with sensitive dopants. More importantly, the sensitive‐dopant‐free 2mF‐X59 based PSCs maintain 95% of their initial performance for more than 500 h under air exposure, showing much better long‐term stability than control PSCs based on Spiro‐OMeTAD with sensitive dopanst. This is the first case that a sensitive‐dopant‐free HTM is demonstrated in PSCs with a high PCE (>18%) and good stability by optimizing the literature HTM. This work could pave a new way to develop low‐cost sensitive‐dopant‐free HTMs for highly efficient and stable PSCs for practical applications.

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“…[ 15–19 ] In particular, use of the modern synthetic methods opens a way for a huge variety of the organic hole‐transporting materials (HTMs), while systematic study of variations could lead to the innovations in the field of molecular electronics. [ 20–24 ]…”

Section: Introductionmentioning

confidence: 99%

Molecular Engineering of Fluorene‐Based Hole‐Transporting Materials for Efficient Perovskite Solar Cells

et al. 2022

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New Spiro‐OMeTAD analogues and the simpler “half” structures with the terminated methoxyphenyl and/or carbazolyl chromophores are successfully synthesized under Hartwig–Buchwald amination conditions using commercially available starting materials. New fluorene‐based hole‐transporting materials combined with suitable ionization energies properly align with the valence band of the perovskite absorber. Additionally, these compounds are amorphous, which is an advantage for the formation of homogenous films, as well as eliminate the possibility for films to crystallize during operation of the devices. The most efficient perovskite solar cells devices contain carbazolyl‐terminated Spiro‐OMeTAD analogue V1267 and reach a power conversion efficiency of 18.3%, along with a short‐circuit current density, open‐circuit voltage, and fill factor of 23.41 mA cm−2, 1.06 V, and 74.0%, respectively. Moreover, “half” structures with methoxyphenyl/carbazolyl fragments show excellent long‐term stability and outperform Spiro‐OMeTAD and, therefore, hold a great prospect for practical wide‐scale applications in optoelectronic devices.

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Synthesis and Properties of Dithiafulvenyl Functionalized Spiro[fluorene-9,9′-xanthene] Molecules

Cited by 30 publications

References 40 publications

Recent Progress in Perovskite Solar Cells Modified by Sulfur Compounds

Recent Progress in Perovskite Solar Cells Modified by Sulfur Compounds

Introduction of Fluorine Into spiro[fluorene‐9,9′‐xanthene]‐Based Hole Transport Material to Obtain Sensitive‐Dopant‐Free, High Efficient and Stable Perovskite Solar Cells

Molecular Engineering of Fluorene‐Based Hole‐Transporting Materials for Efficient Perovskite Solar Cells

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