Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof

Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof

  • CN 102,154,003 B
  • Filed: 02/12/2011
  • Issued: 04/22/2015
  • Est. Priority Date: 02/12/2011
  • Status: Active Grant
First Claim
Patent Images

1. a carbazole abutment fluorescent cyanogen dye probe, is characterized in that:

  • this cyanine dyes probe structure includes carbazole abutment and is bonded in the cyanine dyes probe formed between the benzothiazole of thiazole orange and 4-toluquinoline salt respectively;

    3 side chain one end of described carbazole ring are connected with 2 carbon of benzothiazole, and 6 formyl radicals of the carbazole the other end are connected with 4-vinylquinoline salt compound;

    Described 4-toluquinoline salt is with Br -for the 4-toluquinoline salt of negatively charged ion, the group on the N position of 4-toluquinoline salt is respectively-CH 2cH 2cOOH ,-CH 2cH 2cH 2cH 2cH 2cOOH ,-CH 2cH 3,-CH 2cH 2cH 2br, The characteristic of described carbazole abutment fluorescent cyanogen dye probe;

    Fluorescence emission wavelengths;

    630nm-660nm;

    Stoke shift (Stocks);

    130-151nm;

    Described carbazole abutment fluorescent cyanogen dye probe is prepared by the following method;

    1) preparation of 3-benzothiazolyl-6-formyl radical-N-ethyl carbazole, 3-benzothiazolyl-6-formyl radical-N-benzyl carbazoleRespectively to adding amount of substance in 4 100mL round-bottomed flasks than the N for 1;

    1, dinethylformamide (DMF) and phosphorus oxychloride, drip and finish, after stirring at room temperature to reaction system is blush, drip the 3-benzothiazolyl-N-ethyl carbazole that amount of substance is 17 times of DMF respectively, 1 of 3-benzothiazolyl-N-benzyl carbazole, 2-dichloroethane solution, cumulative volume is at 40-70mL, the return stirring reaction 6h-12h when temperature is 79-80 DEG C, pour into after being cooled to room temperature in frozen water, with dichloromethane extraction, column chromatography for separation is purified, obtain 3-benzothiazolyl-6-formyl radical-N-ethyl carbazole respectively, 3-benzothiazolyl-6-formyl radical-N-benzyl carbazole,2) preparation of carbazole abutment fluorescent cyanogen dye probeRespectively the 4-toluquinoline salt with different substituents on the N position of the 3-benzothiazolyl-6-formyl radical-N-ethyl carbazole of draw through step 11 mole, 3-benzothiazolyl-6-formyl radical-N-benzyl carbazole and four parts 1.5 moles is dissolved in ethanol;

    drip the piperidines with 4-toluquinoline salt equivalent;

    the return stirring reaction times 8-16h when temperature is 75-80 DEG C;

    be cooled to room temperature;

    add ether again and separate out red solid;

    suction filtration;

    filter cake, through column chromatography for separation, obtains described carbazole abutment fluorescent cyanogen dye probe.

View all claims
    ×
    ×

    Thank you for your feedback

    ×
    ×