Aminomethyl-pyrene, release

Then, we synthesized AB6 dendron 31 with six molecules of aminomethyl-pyrene as reporter units and the f-butyloxycarbonyl (Boc) protecting group as a trigger (Fig. 5.23). The dendron was designed to release its six tail units upon removal of the protecting group. 

FIGURE 5.24 Release of aminomethyl-pyrene from dendron 31 upon removal of the Boc protecting group trigger (1 1 MeOH/DMSO mixture with 2% aqueous solution of Bu4NOH) ( ) Control reaction under similar conditions with dendron 31 with the Boc trigger intact (A)-... 

Next, we synthesized a second generation of self-immolative dendron with a similar tail-unit and photo-labUe trigger (Uke compound 25). We repeated the previous experiment and monitored the release of the tail-molecules. It was clearly observed (data not shown) that upon cleavage of the trigger, the self-immolative release of aminomethyl-pyrene is initiated and completed after 21 h. 

Fig. 3 HPLC chromatograms of first generation self-immolative dendron activation to release aminomethyl-pyrene (compound 27 [50 p,M] in methanol with 10% triethylamine). a Before radiation, b After radiation, f = 0. ct = 4h. dt=llh...

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