Structure

N-[2-[(2-bromo-6-cyano-4-nitrophenyl)azo]-5-(diethylamino)phenyl]acetamide

CAS
2537-62-4
Catalog Number
ACM2537624
Category
Main Products
Molecular Weight
459.30
Molecular Formula
C19H19BrN6O3

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Specification

Synonyms
N-{2-[(E)-(2-bromo-6-cyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl}acetamide
Boiling Point
685.2 °C at 760 mmHg
Flash Point
368.2 °C

Disperse Dyes such as Disperse Blue 183:1 Enabling Predictable Persistent Luminescence in Full-Color Afterglow Systems

Schematic diagram and luminescence of RTP materials prepared with dyes such as Disperse Blue 183:1. Xiao, Guowei, et al. Chemical Science 15.41 (2024): 17224-17231.

Achieving predictable full-color ultralong room temperature phosphorescence (RTP) remains a significant challenge for advanced optoelectronic applications. This case study explores the integration of industrial disperse dye, including disperse blue 183:1 (Dye-B), disperse yellow 114 (Dye-Y), and disperse red 145 (Dye-R) within a polymer host-guest system to create tunable, persistent full-color afterglow systems through phosphorescence resonance energy transfer (PRET).
Preparation
This work chose polyurethane (PU) as the polymer matrix and incorporated the unique luminophore tetraacetylethylenediamine (TAED) to create the energy donor PU@TAED, which exhibits a long room-temperature phosphorescent (RTP) lifetime of 1.18 seconds and a wide emission spectrum from blue to red. Subsequently, added three classic disperse dyes-Dye-B, Dye-Y, and Dye-R -to PU@TAED as energy acceptors.
Key Results
This integration led to blue, yellow, and red persistent luminescence with lifetimes of 1.13, 1.1, and 0.9 seconds, respectively, through the photogenerated energy transfer (PRET) process. Utilizing subtractive color mixing theory, a range of predictable full-color afterglow systems in disperse dye-doped PU@TAED was devised, achieving an accuracy of 88.89% in forecasting afterglow colors within the MacAdam ellipses tolerance range. This research offers a viable approach for predicting and creating full-color ultralong RTP and introduces a novel method for on-demand color manipulation in multicolored and machinable materials.

The Photofading Mechanism of Azo Dyes, Such as Disperse Blue 183:1, on Nylon 6 Fabrics

Structure and fading behavior of disperse blue 183:1 and other dyes. Okada, Yasuyo, et al. "Role of thermal reactions in photofading of disperse azo dyes on nylon."

Disperse azo dyes for PET, especially those with nitro groups, exhibit very low light fastness (LF) on nylon 6 (PA). This work investigates the reasons for such LF on PA, using several dyes such as disperse blue 183:1, red 73, and red 1 as models.
Methodology: The photofading of disperse dyes, specifically phenylazo-anilines, -pyridones, -indoles, and -quinolone, on polyamide (PA) fabric was investigated experimentally by analyzing K/S (Kubelka-Munk parameter) spectra derived from reflection data across a wavelength range of 250-700 nm after exposure to a carbon arc in air.
Key Findings
· Dual Fading Pathways: Azo Scission (AS) occurs through thermal reactions between hydrazinyl radicals and monohydrogenated (MHN) dye radicals. Nitrosation (NS) results from reactions between HNS radicals and MHN radicals (concentration-dependent).
· Upon light exposure, azo dyes with nitro groups generate hydrazinyl radicals (from azo groups) and hydroxynitrosyl (HNS) radicals (from nitro groups) via hydrogen abstraction.
· Variations in fading behavior among different azo dyes can be attributed to energy constraints in the thermal reaction pathways of MHN radicals. Despite the lower inherent stability of its N7-radicals compared to N8-radicals in other dyes, DB 183:1's fading rate exceeded that of disperse red 73 due to its reaction energetics and significant HNS radical generation.

What is the molecular formula of the keyword?

The molecular formula of the keyword is C19H19BrN6O3.

What is the molecular weight of the keyword?

The molecular weight of the keyword is 459.3 g/mol.

What is the IUPAC name of the keyword?

The IUPAC name of the keyword is N-[2-[(2-bromo-6-cyano-4-nitrophenyl)diazenyl]-5-(diethylamino)phenyl]acetamide.

What is the InChIKey of the keyword?

The InChIKey of the keyword is KTXMBTRTVMMWQS-UHFFFAOYSA-N.

How many hydrogen bond donor counts are there in the keyword?

There is 1 hydrogen bond donor count in the keyword.

How many hydrogen bond acceptor counts are there in the keyword?

There are 7 hydrogen bond acceptor counts in the keyword.

How many rotatable bond counts are there in the keyword?

There are 6 rotatable bond counts in the keyword.

What is the exact mass of the keyword?

The exact mass of the keyword is 458.07020 g/mol.

What is the topological polar surface area of the keyword?

The topological polar surface area of the keyword is 127Ų.

Is the compound canonicalized?

Yes, the compound is canonicalized.

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