28656-26-0

Upstream product

• 573-97-7 1-bromo-2-naphthol 
• 101597-25-5 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol 
• 108202-36-4 1-(4-methoxyphenyl)naphthalen-2-ol 
• 135-19-3 β-naphthol 
• 101018-40-0 1,1-bis(4-methoxyphenyl)prop-2-en-1-ol 
• 146746-73-8 1-bromo-2-(methoxymethoxy)naphthalene 
• 90-96-0 bis(p-methoxyphenyl)methanone 

Relevant academic research and scientific papers

Spectral manifestation of protonation of photochromic naphthopyrans

The formation of proton complexes of the photoinduced colored open form of naphthopyrans in solutions was first discovered and investigated by spectral-kinetic method. The complexes exhibit a new absorption band in the visible region, which is bathochromically shifted relative to the absorption band of the photoinduced colored open form. With an increase in the concentration of perchloric or hydrochloric acid, this long-wavelength absorption band appears immediately after the addition of acids to solutions of photochromic compounds. The protonation efficiency depends on the strength of the acids.

Functional mesoporous aluminosilicate nanoparticles as host material to fabricate photo-switchable polymer films

Precisely nano-sized aluminosilicate particles (average diameter size 50 to 80 nm) with tailor-made internal surface polarity are suitable as host material for photochromic dyes of the chromene type in order to produce optical transparent photoswitchable polymer films. The sophisticated host material does accomplish two important requirements for a technical application, appropriate internal space for the light induced reversible switching process of the adsorbed dye and suppression of disturbing chemical reactions. The adjustment of the internal surface polarity of the host material was achieved by silane reagents which could be observed by means of specific solvatochromic probes. The Royal Society of Chemistry 2011.

Synthesis and Photochromism of Novel Pyridyl-Substituted Naphthopyrans

Multitarget synthetic strategies to access novel photochromic 3H-naphtho[2,1-b]pyrans decorated with pyridyl units are described. The new pyridyl-substituted 3H-naphtho[2,1-b]pyrans display good photochromic properties with reversible generation of photomerocyanines, which exhibit mainly orange/red hues. Photochromic parameters including photocolorability and persistence of color vary tremendously on structural modification of the naphthopyran core.

An intramolecular, Pd-mediated α-arylation route to 4-aryl-2-naphthols

1-Aryl-1-(2-bromophenyl)but-2-yn-1-ols, obtained from the addition of prop-1-yn-1-yllithium to 2-bromobenzophenones, readily rearrange to 4-aryl-4-(2-bromophenyl)but-3-en-2-ones upon treatment with TFA. Subsequent intramolecular Pd-mediated α-arylation of

Tuning the color switching of naphthopyrans via the control of polymeric architectures

A range of polymerisable photochromic naphthopyrans were prepared via the synthesis of an acrylate moiety on either the naphthalene ring (R) and/or the di-aryl (Ar) rings on the 3-position of the naphthopyran. The monomers obtained (NA) were copolymerised

Observations on the synthesis of photochromic naphthopyrans

1-Naphthol reacts with 1,1-diarylprop-2-yn-1-ols 5a,b, under alumina catalysis, by two pathways to give the photochromic naphtho[1,2-b]pyrans 6a,b, together with the propenylidenenaphthalenones 7a,b, representatives of a new class of merocyanine dyes. With 2-methyl-1-naphthol, formation of the photochrome is suppressed; the only products are merocyanines 7c,d. The cyclocondensation of 2-naphthol with 5a,b proceeds much more efficiently, to give the naphtho[2,1-b]pyrans 14a,b. Pyran formation is not suppressed from either 1-bromo- or 1-(4 -methoxyphenyl)-2-naphthol; reaction with 5a,b merely results in expulsion of the C-1 substituent. An alternative pathway supervenes in the reaction of 1-methyl-2-naphthol with 5a to give the benz[e]indanone 17, the constitution of which was determined by X-ray crystallography. Reaction of the 1,3,3-triarylpropynols 19a,b with 1-naphthol affords the naphthopyrans 20 together with merocyanines 21, whilst the isomeric pyrans 23 are efficiently produced from 2-naphthol. The configuration of merocyanines 7a and 21a was unequivocally established by X-ray crystallography. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Facile One-Pot Synthesis of Photochromic Pyrans

(Equation presented) Photochromic pyrans, including [3H]naphtho[2,1-b] pyrans, [2H]naphtho[1,2-b]pyrans, indeno-fused naphtho[1,2-b]pyrans, and heteroannulated pyrans, were synthesized in excellent yields through a facile one-pot procedure by reaction of propargyl alcohol and naphthol or phenol derivatives in the presence of 5 mol% PPTS and 2 equiv of (MeO)3CH. Symmetrical and nonsymmetrical bispyrans can also be prepared using the protocol.

Photochromic naphthopyran compounds

A naphthopyran compound of general formula (I) STR1 wherein R1 represents a group of the formula --NR2 R3 wherein each of R2 and R3, which may be the same or different, independently represents an alkyl group, or a carbocyclic or heterocyclic group, or R2 and R3 taken together with the nitrogen atom to which they are attached represent a heterocyclic ring having one or more hetero atoms and which may optionally carry at least one substituent selected from alkyl, aryl, or heteroaryl groups; each of R4 and R5, which may be the same or different, independently represents an alkyl, alkenyl, carbocyclic or heterocyclic group, or R4 and R5 taken together with the carbon atom to which they are attached form a carboxylcyclic ring or a heterocyclic ring; and R6 represents a hydrogen atom or a substituent selected from alkyl, alkoxy, aryl, aryloxy, heteroaryl, halogen, a group of formula R1 as defined above, azo, imino, amide, carboxylate, ester, cyano, trifluoromethyl or nitro, and in addition R6 may represent a carbocyclic or heterocyclic ring fused to ring A. The naphthopyran compounds of the invention are useful as photochromic materials in lenses, e.g. sunglasses, and photochromic transparencies for cars and aircraft. The invention also provides, as new intermediate compounds, amine-substituted chloro-naphthols and amine-substituted naphthols.

Photochromic compounds

A naphthopyran compound of general formula (I) STR1 wherein R1 represents an alkyl group or an aryl group; each of R4 and R5, which may be the same or different, independently represents an alkyl, alkenyl, carbocyclic or h