Anthracene, amino

Eused-ring polycycHc fluoroaromatics can be made from the corresponding amino fused-ring polycycHc or from preformed fluoroaromatics, eg, 4-fluorophenyl-acetonitrile [459-22-3] (275). Direct fluorination techniques have been successfully appHed to polycycHc ring systems such as naphthalene, anthracene, benzanthracenes, phenanthrene, pyrene, fluorene, and quinoHnes with a variety of fluorinating agents xenon fluorides (10), acetyl hypofluorite (276), cesium fluoroxysulfate (277), and electrochemical fluorination (278,279). 

This chapter focuses on recent developments in the design and applications of fluorescent organic markers, such as coumarins, benzoxadiazoles, acridones, acridines, polyaromatics (naphthalene, anthracene, and pyrene), fluorescein, and rho-damine derivatives, which display maximum fluorescence emission in the UV/ visible region and have been applied in the labeling of relevant biomolecules, namely DNA, RNA, proteins, peptides, and amino acids, among others. 

The reaction of potassium 3-amino-4-oxo-3,4-dihydroquinazoline-2-thiolate 62 with a-bromophenylacetic acid 63 resulted in the formation of (3-amino-4-oxo-3,4-dihydroquinazolin-2-ylsulfanyl)-phenyl-acetic acid methyl ester 64 which on alkali treatment and subsequent acidification resulted in the synthesis of 2-phenyl- 1-thia-4,4a,9-triaza-anthracene-3,10-dione 65 <1999JCR(S)86>. Similarly, the reaction of potassium 3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- pyrimidine-2-thiolate 66 with a-bromo-ester 67 resulted in the formation of 2-(3-amino-5,6-dimethyl-4-oxo-3,4,4a,7a-tetrahydrothieno[2,3- / pyrimidin-2-ylsulfanyl)-propionic acid ethyl ester 68. Subsequent treatment with alkali followed by acidification resulted in the formation of 2,3,7-trimethyl-3a,9a-dihydro-l,8-dithia-4a,5,9-triazacyclopenta[ ]naphthalene-4,6-dione 69 <2000JHC1161>... 

A wide variety of different classes of fluorescent molecules has been investigated in the peroxyoxalate chemiluminescent systems. Among those screened were fluorescent dyes such as rhodamines and fluoresceins, heterocyclic compounds such as benzoxazoles and benzothiazoles, and a number of polycyclic aromatic hydrocarbons such as anthracenes, tetracenes, and perylenes. The polycyclic aromatic hydrocarbons and some of their amino derivatives appear to be the best acceptors as they combine high fluorescence efficiency with high excitation efficiency in the chemiluminescent reaction [28],... 

No dynamic processes involving intra- or intermolecular transfer of the NH2 group was observed by NMR spectroscopy up to 100 °C (Scheme 23). 1-Amino-1,10-phenanthrolinium cation does not react with 4-methylpyridine and 4-methyl-l,10-phenanthroline with a transfer of the amino group, and it fails to react with mesitylene and anthracene even at elevated temperature. 

In compound (4) (Figure 12.15) the fluorescence of the anthracene group is quenched by electron transfer from both the crown ether unit and the amino group. The electron transfer processes from the crown ether and the amino group can be prevented by adding Na+ and H+, respectively. 

Water colloid solutions of fullerenes C60 (10 4 M) were prepared as described in Scharff et al. (2004). Fullerene-aminopropylaerosyl (fullerene C60-composite-l) was synthesized (Golub et al., 2003) by the introduction of aminopropyl chains oriented ad extra by amine groups (0.9 mM/g), to the surface layer of sihcon dioxide nanoparticles that were bound to fullerene C60 (0.12 mM/g) (Fig. 6.1). Fullerene-anthracenaliminopropylaerosyl (fullerene C60-composite-2) was composed also from anthraccnaliminc (0.2mM/g) that was introduced via azomethine condensation of aldehyde group of anthracenal with surface amino group. 

This type of probe, often called fluorescent photoinduced electron transfer (PET) sensors, has been extensively studied (for reviews, see Refs. 22 and 23). Figure 2.2 illustrates how a cation can control the photoinduced charge transfer in a fluoroiono-phore in which the cation receptor is an electron donor (e.g., amino group) and the fluorophore (e.g., anthracene) plays the role of an acceptor. On excitation of the fluorophore, an electron of the highest occupied molecular orbital (HOMO) is promoted to the lowest unoccupied molecular orbital (LUMO), which enables photoinduced electron transfer from the HOMO of the donor (belonging to the free cation receptor) to that of the fluorophore, causing fluorescence quenching of the latter. On... 

Diazotization of the monoamine in acidic aqueous media formed only the diazoamino compound in high yield. In an attempt to generate and trap 1,2,5-thiadiazyne via diazotization of the 3-amino-4-carboxylic acid in the presence of anthracene, a mixture comprising 9-nitroanthracene and a small amount of 9-thiocyanoanthracene was obtained <71TL2143>. 

---