The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Nov. 25, 2014
Filed:
Oct. 07, 2013
Synthesis of two-photon absorbing polyhydroxy diphenylamino-dialkylfluorene-1,3,5-triazine molecules
The United States of America As Represented BY the Secretary of the Air Force, Wright-Patterson AFB, OH (US);
Loon-Seng Tan, Centerville, OH (US);
Ramamurthi Kannan, Cincinnati, OH (US);
Matthew Dalton, Bellbrook, OH (US);
The United States of America as represented by the Secretary of the Air Force, Wright-Patterson AFB, OH (US);
Abstract
A method of synthesizing a two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound having the structure: where Y is hydrogen, a thermally self-polymerizable acrylic, or a methacrylic group; R is an alkyl group of the formula —CH, wherein the subscript m ranges from 1 to 6, or an alkylether group of the formula —(CHCHO)Me, wherein the subscript p ranges from 1 to 5; R' is an alkyl group; and the R′—(OY)groups are attached to the phenyl rings of the triarylamine moiety either in a para position or a meta position and the subscript x ranges from 1 to 3. The compound may be synthesized by (a) synthesizing a diarylamine intermediate, (b) synthesizing a brominated 1,3,5-triazine intermediate as a three-arm core structure, and (c) forming the two-photon active tris(diarylamino-9,9-di(R)fluorenyl)-1,3,5-triazine compound by covalently joining the diarylamine and each arm of the three-arm core structure and removing the acetone protecting groups. The diarylamine intermediate may be synthesized by protecting tris-1,1,1-(hydroxymethyl)ethane, via a ketal formation with acetone, as an acetonide derivative; furnishing bromophenoxy-methyltrimethyl-1,3-dioxane from the acetonide derivative; and arylating aniline with the bromophenoxy-methyltrimethyl-1,3-dioxane.