Naphthalimide dyes

Naphthalimide Dyes. Derivatives of 4-aminonaphthalimide were used initially to dye acetate fibers. For polyesters, condensation products of 1,8-naphthalenedicar-boxylic acid (e.g., 19) or 1,4,5,8-naphthalenetetracarboxylic acid [128-97-2] with 1,2-diaminobenzenes are used. 

Acenaphthene is a chemical intermediate used to produce naphthalimide dyes, which are used as fluorescent whitening agents, and used in manufacturing plastics, insecticides, and fungicides. 

Uses Chem. intermediate to produce naphthalimide dyes used as fluorescent whitening agents (Japan) prod, of a paper dye Manuf./Distrib. Aldrich http //www.sigma-aldrich.com-, Alfa Aesar http //www.alfa.com, Lancaster Synthesis Supelco http //www.sigma-aidrich.com, TCI Am. http //www.tciamerica. com... 

Grabchev, L, Petkov, C., and Bojinov, V. Infrared spectral characterization of poly (ami-doamine) dendrimers peripherally modified with 1,8-naphthalimides. Dyes and Pigments, 62,229-234 (2004). 

May, B., Poteau, X., Yuan, D., Brown, R.G. A study of a highly efficient resonance energy transfer between 7-N, N-diethylamino-4-methylcoumarin and 9-butyl-4-butylamino-l, 8-naphthalimide. Dyes Pigm. 42, 79-84 (1999)... 

Bromo-N-alkylnaphthalimides undergo aromatic nucleophilic substitution reaction with amines, alkoxides and thiols under microwave irradiation in the presence of KF/AI2O3 under solvent-free conditions to afford a number of fluorescent 4-sub-stituted-l,8-naphthalimide dyes. This is an efficient method for C-N, C-0 and C-S bond formation by applying suitable nucleophiles. Adducts were produced in good to excellent yields (70-95%) and relatively in short times (Bardajee, 2013). 

Stewart, W. W. (1978) Functional connections between cells as revealed by dye-coupling with a highly fluorescent naphthalimide tracer. Cell (Cambridge, Mass.) 14, 741. 

Industrially applied disperse dyes are based on numerous chromophore systems. Approximately 60 % of all products are azo dyes, and ca. 25 % are anthraqui-none dyes, with the remainder distributed among quinophthalone, methine, naphthalimide, naphthoquinone, and nitro dyes [9],... 

The 4-aminonaphthalimides and their /V-alkylatcd derivatives are brilliant greenish yellow fluorescent dyes. A cylation of the amino group at the 4-position of the naphthalimide ring shifts the fluorescence toward blue [111], yielding compounds suitable for use as optical brighteners, such as 4-acetylamino-7V-(//-butyl)naph-thalimide [3353-99-9] [112],... 

Photoreduction of benzophenone by primary and secondary amines leads to the formation of benzpinacol and imines [145]. Quantum yields greater than unity for reduction of benzophenone indicated that the a-aminoalkyl radical could further reduce the ground state of benzophenone. Bhattacharyya and Das confirmed this in a laser-flash photolysis study of the benzophenone-triethylamine system, which showed that ketyl radical anion formation occurs by a fast and a slow process wherein the slow process corresponds to the reaction of a-aminoalkyl radical in the ground state of benzophenone [148]. Direct evidence for similar secondary reduction of benzil [149] and naphthalimides [150] by the a-aminoalkyl radical have also been reported. The secondary dark reaction of a-aminoalkyl radicals in photo-induced electron-transfer reactions with a variety of quinones, dyes, and metal complexes has been studied by Whitten and coworkers [151]. 

The heavy-atom eontaining dyes are based on 3-bromo-4-alkylamino-N-alkyl-l, 8-naphthalimide. These are yellow dyes that absorb blue light, and are similar to the optical brighteners used in washing powders. 

The bromine-containing dyes were prepared by Lewis and Uteeht which are described here A. 3-Bromo-4 (hexylamino)-N-hexyl-l, 8-naphthalimide... 

Cellulose. Cellulose has been used as a solid powdered substrate for the study of photophysical and photochemical studies of several organic probes, mostly dyes. Some of the properties of this substrate, namely the capacity of adsorbing molecules both by entrapment and on the surface of the natural polymer (forming in many cases hydrogen bonds) and also the absence (or extremely reduced) of diffusion of oxygen, make this substrate a particularly attractive one for room temperature luminescence studies [75-83]. We recently published some fluorescence and phosphorescence studies of rhodamine dyes [15,81,82], auramine O [81b], 2,3-naphthalimides [84], oxazine [85], acridine orange [86], and cyanine dyes [16, 87, 88] adsorbed on cellulose. 

Merck Index Number 5594 Chemical/Dye Class Naphthalimide Molecular Formula Ci3H9Li2N509S2 Molecular Weight 457.25 Physical Form Orange powder Solubility Soluble in water soluble in ethanol Melting Point >200 °C Absorption (Amax) 280 nm, 428 nm Emission (Aroax) 540 nm... 

Solid-supported Hg sensor incorporating a piperazine-pyridine functionalised naphthalimide fluorophore has been attached to mesoporous SBA-15 silica and shown to have a selective fluorescence response for Hg ". Interestingly, the selectivity for Hg was found to be higher than for the precursor alkynyl dye however, the click triazole was not proposed to be involved in coordination to the metal ion in the active system [45]. 

Methodology to functionalise two separate oligodeoxyribosenucleotides with a terminal azide and an aUcyne-terminated naphthalimide which form a fluorescent triazole-containing dye in the presence of Cu" has been shown to be effective in the detection of the correct complementary DNA template. Whilst the click triazole formation was slow in the absence of the template, a significant enhancement was observed in the presence of the correct complementary template, resulting in a rapid increase in fluorescence, whereas a template with only a single nucleotide mismatch did not [104]. 

---