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**10H-Phenoxazine, 10-(4-methoxyphenyl)-** is a strong electron-donating aromatic amine used in the design of nonlinear optical chromophores and dye-sensitized solar cells (DSSCs). In nonlinear optical applications, it exhibits significantly enhanced electron-donating ability compared to traditional donors, leading to a reduced energy gap, higher molecular quadratic hyperpolarizability (μβ), and improved electro-optic activity (e.g., larger *r*33 values). In DSSCs, its incorporation as an N-substituent in phenoxazine-based dyes helps suppress charge recombination, improving open-circuit voltage, though it may reduce dye adsorption on TiO2 due to steric effects. Overall, its structural features contribute to high-performance optoelectronic materials. **Other names:** N-(4-Methoxyphenyl)phenoxazine.

58736-67-7

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58736-67-7 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 58736-67-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,7,3 and 6 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 58736-67:
(7*5)+(6*8)+(5*7)+(4*3)+(3*6)+(2*6)+(1*7)=167
167 % 10 = 7
So 58736-67-7 is a valid CAS Registry Number.

58736-67-7Downstream Products

58736-67-7Relevant academic research and scientific papers

Comparative studies on structure-nonlinearity relationships in a series of novel second-order nonlinear optical chromophores with different aromatic amine donors

Liu, Fenggang,Yang, Yuhui,Wang, Haoran,Liu, Jialei,Hu, Chaolei,Huo, Fuyang,Bo, Shuhui,Zhen, Zhen,Liu, Xinhou,Qiu, Ling

, p. 347 - 356 (2015)

A series of second-order nonlinear optical chromophores containing an identical π-bridge and electron acceptor but different, aromatic amine electron-donating groups have been synthesized and systematically investigated. The donors studied here include traditional donors carbazole, triphenylamine and N,N-diethylaniline and novel donor phenothiazine, phenoxazine and N-(4-methoxyphenyl)phenoxazine. The ultraviolet absorption, solvatochromic, redox properties, density functional theory calculations, thermal stabilities and electro-optic activities of these chromophores were systematically studied to compare the strength of the donors and illustrate the structure-performance relationships within six chromophores. The results show that the new donors have stronger electron-donating ability than traditional donors. Moreover, they show reduced energy gap, much larger molecular quadratic hyperpolarizability (μβ) and r33 value. Exemplified by the N-(4-methoxyphenyl)phenoxazine chromophore, it showed nearly three times higher μβ and more than four times higher r33 value than that of the N-hexylcarbazole containing chromophore.

The effects of the number of anchoring groups and N-substitution on the performance of phenoxazine dyes in dye-sensitized solar cells

Lee, Woosung,Yuk, Sim Bum,Choi, Jun,Kim, Hae Jung,Kim, Hyun Woo,Kim, Se Hun,Kim, Boeun,Ko, Min Jae,Kim, Jae Pil

, p. 13 - 21 (2014)

Four novel phenoxazine-based organic sensitizers were synthesized and applied to dye-sensitized solar cells. Cyanoacrylic acid as an additional anchoring group was introduced to the phenoxazine for efficient electron extraction from the donor part, and an N-substituent was added to suppress dye aggregation. The photophysical, electrochemical and photovoltaic properties of the solar cells based on these dyes were investigated to study the effects of these substituents on the performance of the dye-sensitized solar cells. The additional cyanoacrylic acid acceptor improved the short-circuit current because it widened the absorption ranges of the dyes, although it also increased the recombination rate. The N-methoxyphenyl unit decrease charge recombinations, resulting in higher open-circuit voltage. However, the bulky substituent decreased the amount of dye absorbed on the TiO2. As a result, the fabricated cells with the four dyes exhibited similar overall conversion efficiencies and, of these cells, the solar cell based on the N-4-methoxyphenyl mono-cyanoacrylate substituted dye showed the highest conversion efficiency of 5.09% (short-circuit current = 10.11 mA/cm2, open-circuit voltage = 690 mV, fill factor = 72.23%, an overall conversion efficiency = 5.09% under AM 1.5G conditions).

Effects of introducing functional groups on the performance of phenoxazine-based dye-sensitized solar cells

Bae, Jong Hyuk,Lim, Seung Ju,Choi, Jun,Yuk, Sim Bum,Namgoong, Jin Woong,Ko, Jae Hoon,Lee, Woosung,Kim, Jae Pil

, p. 905 - 915 (2019)

Phenoxazine dyes with a hexyloxy chain and furan moiety were synthesized and used in dye-sensitized solar cells. The dyes were designed to investigate the effects of these substituents on the photophysical and electrochemical properties of the dyes and on cell photovoltaic performance. The introduced hexyloxy moiety, as an additional donor, improved the short-circuit current and open-circuit voltage of the cell by increasing light absorption and steric hindrance, respectively. The furan moiety introduced in the phenoxazine dye as a bridge unit led to a bathochromic shift of the absorption band and a large amount of dye adsorption, increasing the short-circuit current of the cell. Among the synthesized dyes, those with the furan moiety showed the best conversion efficiency of 6.34%.

Light-emitting film and preparation method thereof, light-emitting device and display device

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Paragraph 0112-0115, (2021/10/27)

The invention provides a light-emitting film and a preparation method thereof, a light-emitting device and a display device, and relates to the technical field of display. The light-emitting film is used as a light-emitting layer in the light-emitting device, and the light-emitting film comprises a thermally activated delayed fluorescent material; the thermally activated delayed fluorescent material comprises a donor group, an acceptor group and a linking group, the donor group and the acceptor group are respectively bonded with the linking group, and the general formula of the thermally activated delayed fluorescent material is shown in the specification, wherein Y is a non-conjugated group; and at least one of X1, X2 and X3 is a nitrogen atom. The light-emitting device prepared from the light-emitting film has the advantages of high light-emitting efficiency, high device stability, simple preparation process and low efficiency roll-off.

Hole transport material with phenoxazine as core structure, and synthetic method and application thereof

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Paragraph 0043-0046, (2019/02/17)

The invention belongs to the technical field of organic functional materials, and discloses a hole transport material with phenoxazine as a core structure, a preparation method thereof, and application of the hole transport material in perovskite solar cells. The hole transport material with the phenoxazine derivative as the core structure, two end of which are connected with N,N-dimethoxyaniline,has the advantages of stable natural condition, low cost, high hole mobility, high electric conductivity and the like; the hole transport material with phenoxazine as a core structure has lower production cost and comparable photoelectric conversion efficiency as compared with a conventional hole transport material Spiro-OMeTAD; the novel hole transparent material with phenoxazine as a core structure has a broad application prospect, providing a new choice for manufacture of efficient and stable perovskite solar cells in terms of hole transport materials.

Pd-Catalyzed double N-arylation of primary amines to synthesize phenoxazines and phenothiazines

Zhang, Lu,Huang, Xin,Zhen, Shan,Zhao, Jing,Li, Heng,Yuan, Bingxin,Yang, Guanyu

, p. 6306 - 6309 (2017/08/10)

An efficient and versatile Pd-catalyzed tandem C-N bond formation between aryl halides and primary amines is developed. The transformation allows a one-pot synthesis of phenoxazine and phenothiazine derivatives with a broad range of substitution patterns from readily available precursors.

A general route for synthesis of N-aryl phenoxazines via copper(i)-catalyzed N-, N-, and O-arylations of 2-aminophenols

Liu, Nan,Wang, Bo,Chen, Wenwen,Liu, Chulong,Wang, Xinyan,Hu, Yuefei

, p. 51133 - 51139 (2014/12/10)

A novel copper(i)-catalyzed tandem reaction of N- and O-arylations of 2-[N-(2-chlorophenyl)amino]phenols was developed, by which a series of structurally novel N-aryl phenoxazines were synthesized efficiently. This success owes much to the discovery of hi

Anthrancene derivative compound and organic light-emitting device including the same

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Page/Page column 21-22, (2010/06/11)

Provided is an anthracene derivative compound represented by Formula 1 below and an organic light-emitting device using the same: wherein Ar1, Ar2, R1, R2, R′, m, n, j, k, and X are as defined in the specification. The anthracene derivative compound is advantageously used in the production of an organic light-emitting device with better driving voltage, efficiency, and color purity.

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