218-02-0

Upstream product

• 90-12-0 1-Methylnaphthalene 
• 26842-00-2 phenanthrene-2-carbaldehyde 
• 608519-15-9 (2-phenanthren-1-yl-ethyl)carbamic acid ethyl ester 
• 608519-08-0 3,4-dihydro-2H-naphtho[2,1-f]isoquinolin-1-one 
• 472986-97-3 2H-naphtho[2,1-f]isoquinolin-1-one 
• 100-42-5 styrene 
• 53500-08-6 trans-1-(1-naphthyl)-2-(3-pyridyl)-ethylene 
• 608519-11-5 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline 
• 58794-11-9 cis-1-(1-naphthyl)-2-(3-pyridyl)-ethylene 
• 105654-03-3 2-Aza-4,4-dimethoxy-1-(2-phenanthryl)-1-butene 

Relevant academic research and scientific papers

The photochemical cyclodehydrogenation route to polycyclic azaarenes

This paper reports an investigation of photochemical cyclodehydrogenation for the preparation of polycyclic azaarenes. Various naphthoquinolines and naphthoisoquinolines were obtained from 2-, 3-, and 4-[2-(1- and 2-naphthyl)vinyl]pyridine. 4-[2-(3-Phenanthryl)vinyl]pyridine gave pyreno[1,10-hij]isoquinoline. An efficient preparation of (2-arylvinyl)pyridines is described. Georg Thieme Verlag Stuttgart.

Tuning the nature of the fluorescent state: A substituted polycondensed dye as a case study

An extensive spectroscopic analysis is presented of an elongated polycondensed dye with a donor-acceptor substitution. The charge-transfer (CT) state, polarized along the long molecular axis, is close in energy to a local excitation (LE) of the polycondensed system, roughly polarized along the short molecular axis, which makes this system particularly suitable to investigate the subtle LE/CT interplay. An essential-state model is presented that quantitatively reproduces absorption and fluorescence spectra, as well as fluorescence emission and excitation anisotropy spectra collected in solvents of different polarity and viscosity, which sets a sound basis for the understanding of how solvent polarity and solvent relaxation affect the nature of low-lying excitations. The markedly different fluorescence emission and excitation anisotropy spectra measured in glassy and liquid polar solvents unambiguously demonstrate the major role played by solvent relaxation in the definition of fluorescence properties of the dye. Charge-transfer or local excitations? Fluorescence emission from a substituted azachrysene chromophore is shown to change its nature according to solvent polarity. The different polarization of the low-energy local and charge-transfer excitations (see scheme) is responsible for highly informative fluorescence anisotropy spectra. Experimental results are interpreted and reproduced based on an original three-state model. Copyright

Heck-mediated synthesis and photochemically induced cyclization of [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters and 2-styryl-benzoic acid methyl esters: Total synthesis of naphtho[2,1f]isoquinolines (2-azachrysenes)

We describe two new closely related total syntheses of naphtho[2,1-f]isoquinolines. The first synthesis consists of a Heck coupling reaction between trifluoromethanesulfonic acid 2-(2-ethoxycarbonylaminoethyl)phenyl esters and styrenes to give [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters. These compounds cyclize to give (2-phenanthren-1-yl-ethyl)carbamic acid ethyl esters, from which 2-azachrysenes can be obtained in a three-step sequence. The second synthesis includes a new total synthesis of 2-styrylbenzoic acid methyl esters by Heck coupling of methyl o-iodobenzoates to styrenes, followed by the transformation of the resulting benzoic acid derivatives into phenanthrene-1-carboxylic acid methyl esters and then into the target compounds by a six-step sequence including a Bischler-Napieralski cyclization.

Palladium-mediated total synthesis of 2-styrylbenzoic acids: A general route to 2-azachrysenes

We describe a new total synthesis of 2-styrylbenzoic acids by Heck coupling of methyl o-iodobenzoates to styrenes. Additionally, in the first general synthesis of naphtho[2,1-f]isoquinolines, these acids were transformed into phenanthrenoic acids and then

1-Azabenzanthracene and 9-Azabenzanthracene

The synthesis of 1-azabenzanthracene and 9-azabenzanthracene are presented.

PHOTOCHEMISTRY AND LUMINESCENCE OF ROTATIONAL ISOMERS OF 1-(n-NAPHTHYL)-2-(3-PYRIDYL)ETHYLENE

The trans isomers of 1-(n-naphthyl)-2-(3-pyridyl)ethylene (n,3-NPE, with n=1 or 2) exibit some anomalies in their fluorescence behaviour.The fluorescence spectrum and quantum yield of 2,3-NPE at room temperature show a dependence on the excitation wavelength (λex) and the fluorescence decay follows a bi-exponential function.For 1,3-NPE, only the fluorescence spectrum in a rigid matrix depends on λex whilst ΦF changes only slightly and the observed decay is monoexponential.This behaviour, which can be accompained by a λex-dependent photochemistry, is probably due to the existence in solution of distinct rotational isomers involving the quasi-single bonds between the aromatic groups and the ethylenic carbons.The almost isoenergetic naphthyl conformers are probably responsible for the more pronounced λex-effect on 2,3-NPE while the pyridyl conformers could give a greater contribution to the smaller effect observed in the less planar 1,3-NPE.The corresponding cis isomers give azabenzophenanthrenes as photocyclization products.In both cases, two products were isolated.Their very different chemical yields depend on the position of the heteroatom with respect to the photoreactive site.The fluorescent properties of the four cyclized products, including the effect of oxygen, were also determined.