Synthesis and application of asymmetric aza diisoindole methylene compound and fluorine-boron compound thereof

• Main Authors: LI CHENGHUI, LAI JIANCHENG, YOU XIAOZENG, ZHENG WEI
• Format: Patent
• Language: English
• Published: 23.12.2015
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; ADHESIVES; CHEMISTRY; DYES; HETEROCYCLIC COMPOUNDS; INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIRCHEMICAL OR PHYSICAL PROPERTIES; MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FORELSEWHERE; MEASURING; METALLURGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; NATURAL RESINS; ORGANIC CHEMISTRY; PAINTS; PHYSICS; POLISHES; TESTING

The present invention relates to synthesis and application of an asymmetric aza diisoindole methylene compound and a fluorine-boron compound thereof. The compound and fluorine-boron compound thereof provided by the present invention has the characteristics of high yield of fluorescent quantum, large molar extinction coefficient, and large Stokes displacement. In addition, because of its unique "electron donor-pi conjugated system-electron acceptor" asymmetric structure, the compound provided by the present invention shows discoloration and fluorescence quenching phenomena after dropwise addition of strong acid, such as trifluoroacetic acid or trifluoromethyl sulfonic acid, in solvents free of N and O, such as methylene chloride solvent; after addition of organic solvent or compounds containing N or O, the colorless solution can restore its original color and fluorescence, thus the compound can be used to detect substances containing N or O atoms. Meanwhile, the asymmetric aza diisoindole methylene compound and fluorine-boron compound thereof provided present invention have important application values in fluorescence sensing, cell imaging and photodynamic therapy.