1, 8-naphthalimide derivatives

Poly (amidoamine) dendrimers (PAMAM) are new interesting class of star polymers. They have mono dispersive, well defined and developed three-dimensional structures comprising functional groups at high concentration. In its core they have amidic groups. Structurally modified PAMAM dendrimers with 1,8-naphthalimide derivatives are fluorescent dendrimers and they can be applied as effective and selective sensors for different metal cations and protons in organic solvents. This property can be nansferred to other polymer matrixes (for example textiles). 

In this study we present our first results about the possibility for the incorporation of bio-receptors into some new PAMAM dendrimers. Dendrimers under smdy contain peripherally bonded 1,8-naphthalimide derivatives (Figs. 1 and 2). 

The photophysical and photochemical properties of functionalized 1,8-naphthalimide derivatives has been repeatedly investigated. Recent applications in photobiology, such as DNA targeting, anticancer and cellular imaging agents have been reviewed and has led in some cases to clinical trials. Photochemical reactions include mygen sensitization, as recently demonstrated with a water soluble derivative. ... 

Z H.(2011). Synthesis of new 1,8-naphthalimide derivatives with potential antihyperlipidemic activities. (Under publication). 

At one time disperse-type FBAs, such as pyrazoline, coumarin or naphthalimide derivatives, were commonly used to brighten acrylic fibres. Today all the important brighteners for these fibres are cationic in character and can be divided into two main categories ... 

Scheme 8 Naphthalene diimide (18), pyrazinonaphthalimide (19), and bis pyrazino-naphthalimide derivatives (20, 21).

Martin, E., Tones-Costa, V., Martin-Palmar, J., Bousono, C., Tutor-Sanchez, J., and Martinez-Duart, J.M. 2006. Photoluminescence of naphthalimide derivatives deposited onto nanostructured porous silicon. Journal of the Electrochemical Society 153, D134-D137. 

It was shown (Scarlata and Ors, 1986) that there was an increase in polarization of the probe molecule (a 4-amino naphthalimide derivative) during the photoinitiated cure of an acrylate-based coating formulation as the viscosity increased. 

We recently reported the switchable supramolecular self-assemblies on the basis of interaction between melamine group containing photochromic diarylethene unit (DTE) and naphthalimide derivate (33) with similar triple hydrogen bonds (Fig. 3.27). The gel morphology and the contact angels of the xerogel could be facilely tuned by the ratio of DTE and light stimulus [68]. 

Naphthalimide derivatives with therapeutic characteristics A patent review 13EOT299. 

Peroxidized lipids and proteins in lysosomes of the brain cells are reported to result in Alzheimer disease. In this regard, the imaging of H2O2 in lysosomes is important however, it is still very challenging. Recently, Yin and Yoon et at reported a naphthalimide derivative 40 as a selective fluorescent probe for detection of H2O2 in lysosomes, in which a /7-dihydroxyborylbenzyloxy-carbonyl moiety and a morpholine moiety were introduced as a transponder... 

Table 1 (3,4-Epoxycyclohexane)methyl 3,4-epoxycyclohexylcarboxylate (EPOX) conversions obtained under air upon exposure to different visible or blue light sources for 800 s in the presence of naphthalimide derivative/Ph2l" (0.5%/2%, w/w) or naphthalimide derivative/Ph2l //V-vinylcarbazole (0.5%/2%/3%, w/w/w).

Fig. 6 Naphthalimide derivatives. (A) Photopolymerization profiles of an EPOX/TMPTA blend (50%/50%, w/w) in the presence of ND10/Ph2l + /NVK (0.5%/2%/3%, w/w/w) under air (a) and in laminate (b) upon the blue LED at 462 nm exposure (B) photopolymerization profiles of trithiol/DVE-3 blend (40%/60%, n/n 57%/43%, w/w) in laminate in the presence of NDIO/Phal (0.5%/2%, w/w) upon the laser diode at 457 nm exposure curve 1 DVE-3 (vinyl double bond) conversion, curve 2 trithiol (S-H) conversion...

Other Heterocyclic Systems. Naphthalimides (15), where R = —NHCOR, are derivatives of 4-anTinonaphthalimide (69) and are used in plastics. The alkoxynaphthalimides (15, R = OCH ) (70,71) are of particular interest as fluorescent whitening agents. 

Naphthalimides are prepared from naphthaUc anhydride obtained from naphthalene-1,8-dicarboxyhc acid, ie, the oxidation product of acenaphthene or its derivatives, by reaction with amines. They are utilized for synthetic fibers such as polyesters. 

In general and as expected, brighteners of relatively small molecular size are most suitable for application by exhaustion. Less volatile compounds of larger molecular size tend to be preferred for pad-thermosol application or for incorporation in the polymer mass. Commercially important for exhaust application are the previously mentioned pyrene derivative 11.22, the naphthalimide 11.23, the bis(benzoxazolyl)ethene 11.35, the bis (benzoxazolyl) thiophene 11.36, the distyrylbenzene 11.37 and the stilbene bis (acrylic ester) derivative 11.38. Products of the 11.35 type show excellent light fastness but only moderate fastness to sublimation. In view of this volatility they can be used in the transfer printing of polyester. 

The naphthalimide 11.23 is manufactured from acenaphthene by sulphonation, oxidation to the naphthalic anhydride derivative and conversion to 4-methoxy-N-methylnaphthal-imide as outlined in Scheme 11.14. 

Synthesis of the coumarin derivative 11.58 containing two isomeric triazolyl rings is indicated in Scheme 11.24- The substituted pyrazolyl derivative of naphthalimide 11.59 is prepared by a reaction sequence somewhat similar in principle to that already shown in Scheme 11.14, using 4-amino-1,3,5-trimethylpyrazole in the penultimate step followed by quaternisation. 

Since their commercial introduction during the 1940s as components of proprietary detergents and laundry preparations, these products have found extensive usage in the whitening of paper and textile materials. Disperse FBAs are available for whitening hydrophobic fibres and solvent-soluble FBAs impart fluorescence to oils, paints, varnishes and waxes. Approximately 75% of commercially established FBAs are stilbene derivatives with inherent substantivity for paper and cellulosic textiles, but the remainder come from about twenty different chemical classes. These include aminocoumarins (6%), naphthalimides (3%), pyrazoles and pyrazolines (each about 2%), acenaphthenes, benzidine sulphones, stilbene-naphthotriazoles, thiazoles and xanthenes (each about 1%). FBAs of these and other chemical types are discussed in detail in Chapter 11 of Volume 2. 

In the case of the naphthalimide fluorescent brightening agents (98) the most important commercial derivatives are the 4-alkoxy and 4-acylamino (e.g. R is methoxy). Substituent R is usually an alkyl group or an aminoalkyl group capable of quaternization. Thus the most interesting of the series is 4-methoxy-Af-methylnaphthalimide, which is an excellent product suitable for application to a variety of synthetic fibres. 

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