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[ CAS No. 189367-54-2 ] {[proInfo.proName]}

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Chemical Structure| 189367-54-2
Chemical Structure| 189367-54-2
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Jacob B. Hoffman ; Daniel D. Astridge ; So Yeon Park , et al. DOI:

Abstract: As lead halide perovskites (LHPs) continue to achieve success as a light-harvesting material in perovskite solar cells (PSCs), exploring and understanding other materials in the device stack become increasingly important. Particularly, selection of suitable hole transport materials (HTMs) that demonstrate high performance and stability is imperative in the design of P–I–N PSCs. Presented here are a family of 12 structurally related polymers based on either fluorene or carbazole main chains with select aromatic side groups that introduce tunable properties for use in PSCs. How properties such as the highest occupied molecular orbital energy level, conductivity, glass-transition temperature, and wettability of the HTM affect the PSC performance is explored. Devices that incorporate the polymer HTMs perform well relative to PTAA in benchmark P–I–N PSC architectures while exhibiting similar or superior stability under accelerated aging studies. The relative synthetic simplicity and resultant performance of the HTMs in PSCs coupled with the ability to customize properties with different functional groups demonstrates the potential of this family of HTMs for a variety of LHP materials.

Keywords: perovskite solar cells ; hole transport materials ; polymers ; Buchwald?Hartwig coupling ; device stability ; tunable HOMO ; carbazole fluorene

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Astridge, Daniel D ;

Abstract: Perovskite solar cells (PSCs) have demonstrated remarkable efficiency growth in their brief history, and are considered to be of exceptional potential for commercialization due to their excellent absorption properties, varied deposition methods, and compatibility with other solar technologies. Furthermore, perovskites are demonstrating high potential for other applications, such as perovskite light emitting diodes (Pero-LEDs), lasers, and radiation detectors. Most perovskite based devices use hole transporting materials (HTMs) to assist in charge separation and current generation. The three main categories of HTM are inorganic materials, small organic molecules, and polymeric materials. Organic materials typically provide the highest efficiencies for these devices, but have several drawbacks including low economic viability, lack of flexibility for use with the various perovskite absorber layers (PALs), and difficulty of application in the multiple device architectures that exist for these devices. This dissertation primarily describes the design and synthesis of new polymeric materials to improve the processibility and interfacial interactions of HTM and PAL, leading to high efficiency, high stability, and low cost PSCs. Our current research into HTMs takes a four-pronged approach; We found that utilizing the Buchwald-Hartwig amination protocol using primary aryl amines and aryl dihalides afforded highly reproducible, high yielding family of polymers, which could be purified by a simple sequence of precipitations. Appropriate selection of pendant functional groups, such as electron donating methoxy, or electron withdrawing fluorine, allowed for highest occupied molecular orbital (HOMO) tuning, as did the utilization of electron rich carbazole versus the neutral fluorene in the polymer backbone. Control of the glass transition temperature (Tg), a characteristic vital to extended lifetime at elevated temperature, was demonstrated by manipulation of the alkyl side chains in the polymer, which allowed for a balance of solubility and improved Tg. Finally, side chain engineering of the polymers, incorporating more hydrophilic functional groups, was explored to improve the processibility of the PAL on top of the polymer HTMs. This allowed for the manufacture of devices that did not require an interfacial layer or UV/Ozone treatment to form a consistent perovskite film, removing a variable in the device, as well as reducing processing time and cost

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Daniel D. Astridge ; Jacob B. Hoffman ; Fei Zhang , et al. DOI:

Abstract: The development of low-cost materials for charge-selective contacts that provide good energetic alignment with perovskite active layers, favorable thermal properties, and lead to efficient photoconversion is becoming an increasingly important aspect of the perovskite solar cell (PSC) field. Presented here is a series of polymers based on a one-pot polymerization of aryl dihalides with primary aryl amines to produce solution-processable polymers in high yield, with simple purification, and promising properties for high performing P-I-N PSC devices. How these properties can be tuned by careful selection of the reactant chemical moieties is discussed. Through this strategy, a wide range of relevant properties such as glass transition temperature, highest occupied molecular orbital tuning, and polydispersity are explored. When implemented into devices using a triple-cation FAMACs perovskite active layer, the hole transport material series shows average power conversion efficiencies (PCE) in excess of 17%, which is comparable to controls using state-of-the-art poly(triarylamine). How different synthetic parameters such as the reaction time and purification protocol impact device performance is also investigated.

Keywords: polymer HTM ; Buchwald?Hartwig coupling ; perovskite solar cells ; carbazole ; fluorene ; tunable HOMO

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Product Details of [ 189367-54-2 ]

CAS No. :189367-54-2 MDL No. :MFCD03427215
Formula : C25H32Br2 Boiling Point : -
Linear Structure Formula :(C6H13)2C13H6Br2 InChI Key :OXFFIMLCSVJMHA-UHFFFAOYSA-N
M.W : 492.33 Pubchem ID :3539647
Synonyms :

Calculated chemistry of [ 189367-54-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.52
Num. rotatable bonds : 10
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 127.86
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -1.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.63
Log Po/w (XLOGP3) : 11.22
Log Po/w (WLOGP) : 9.42
Log Po/w (MLOGP) : 7.68
Log Po/w (SILICOS-IT) : 9.72
Consensus Log Po/w : 8.74

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -9.63
Solubility : 0.000000115 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble
Log S (Ali) : -11.19
Solubility : 0.0000000032 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -11.53
Solubility : 0.0000000014 mg/ml ; 0.0 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.63

Safety of [ 189367-54-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:
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