By Crano J.C., Guglielmetti R.J.
This quantity deals an in depth exam of the synthesis and particular photochromic houses of the best-known photochromic and thermochromic compounds. It comprises a variety of physico-chemical equipment through which photochromic ingredients should be studied, in addition to functional details. content material: Preliminaries; Contents; creation; 1. Spiropyrans; 2. Spirooxazines; three. Benzo and Naphthopyrans (Chromenes); four. Fulgide relations Compounds: Synthesis, Photochromism, and functions; five. Diarylethenes with Heterocyclic Aryl teams; 6. Photochromism of Dihydroindolizines and similar structures; 7. Photochromic Quinones; eight. Perimidinespirocyclohexadienones; nine. Photochromism by way of Electron move: Photochromic Viologens; Index. summary: This quantity deals an in depth exam of the synthesis and particular photochromic houses of the best-known photochromic and thermochromic compounds. It contains a number of physico-chemical equipment wherein photochromic components might be studied, in addition to useful info
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Additional resources for Organic Photochromic and Thermochromic Compounds, Volume 1 : Photochromic Families
4. Substitution in Spiropyrans The spiropyrans can be brominated with N-bromosuccinimide (NBS) in chloroform to give various substitution patterns that are dependent upon the nature of the two halves of the molecule. In the case of 5-methylspiro-[5,6-dihydrophenanthridine-6,2'(2H-1-benzopyran)], two bromine atoms enter only the chromene but not the phenanthridine portion to give the 6',8'-dibromo derivative (λ max 540nm). In the case of the BIPS compounds, more possibilities occur. Bromination of the unsubstituted BIPS occurs first only in the indoline ring to give a 77% yield of the 5'-bromo compound, then threefold simultaneously in the indoline and chromene rings to give 60% overall yield of the 5',7',6,8-tetrabromo compound.
Intermediates for Spiropyrans The salicylaldehyde and hydroxynaphthaldehyde intermediates are often prepared by introducing a formyl group or an equivalent synthon next to the OH group (blocked, if necessary) of the corresponding phenol or naphthol; many formylation methods are known. Salicylaldehydes can easily undergo the common electrophilic substitution reactions, thus affording, for example, nitrated, halogenated, and chloromethylated products suitable for further transformations. The two complications arise with simple substitutions, however.
Nitration (79%) and hydrolysis gave the isomeric 6-aminomethyl-5-nitro compound. 46 The aminomethyl group is a useful link to polymers, sensitizers, initiators, etc. Fischer’s aldehydes having a 2-hydroxyethyl or 2-chloroethyl substituent on the N atom and a 5-nitro substituent were prepared by formylation of the corresponding 2,3,3-trimethylindoline[1,2]-b]oxazines. According to the NMR and IR spectral evidence, the aldehydes, both in solution and the solid state, existed entirely in the open chain form rather than as 2-formylmethyl-2,3,-dimethylindolino[1,2- b]oxazines.