Development of Sensitizers and Chemiluminescent Reagents intending to create new Super-function

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We have explored function-accumulating system for generation of a new super-function. Recently many investigations on chemo-sensors as the super-function have employed chelation-enhanced fluorescence. However, metal ion-based functional chemi luminescent systems have not been reported for the lophines. We presented the first potential signaling system incorporating a chelating ability and CL property. We have prepared 4,5-diphenyl-2-(2-pyridyl)-imidazole and developed to 2-(2-hydroxyphenyl)-4,5-diphenylimidazole 1 bearing a chelating function. The CL efficiency of 1 was 0.28 times that of lophine peroxide on initiation with KOH/MeOH. When the trigger base was changed to TBAF/THF, the efficiency was 530-fold in dry DMF. Singlet oxygen was detected from the reaction of lophine hydroperoxides in the presence of a singlet oxygen detector. In order to examine the substituent effect on the formation of singlet oxygen, 2-(p-substituted phenyl) lophine peroxides were tested. An electron-attracting group contributed to the efficient formation of singlet oxygen, while an electron-donating group enhanced the chemiluminescence. As the second example, a 2,11-diaza[3,3]paracyclo(9,10)anthracenophane derivative possessing an ethylenediamine host function has been prepared.Further we reported a unique-unexpected rearrangement from [benzene anthracene]biplanemers to energy-stored compounds and a azepine chemistry as a side work.We have achieved outstanding research goals in their functional chemistry and photochemistry of biplanemers as shown above. We are very much grateful for the financial support from the KAKEN fund.