A chemically-responsive bis-acridinium receptor

Abstract

The recognition and the chemical-response properties of a bis-acridinium triphenylene receptor were investigated.

Self-complementary and narcissistic self-sorting of bis-acridinium tweezers

“…Noteworthy, chemical shifts of the acridinium protons of (2)2•4Cl ((H1/8) = 7.26, (H2/7) = 7.32, (H3/6) = 8. 16 and (H4/5) = 8.48 ppm) are similar to (1)2•4Cl in water ( Fig. 1c-d).…”

“…10-Methyl-9(10H)acridone and 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzene were synthesized according to previously reported procedure. 16 All compounds were synthesized using schlenk technics and were fully characterized by 1D ( 1 H, 13…”

“…15 The bis-boronic ester derivative (3) was prepared in 96% yield starting from 1,3-dibromobenzene as previously reported. 16 Compound 3 was then allowed to react in a palladium-catalysed Csp2-Csp2 coupling with 2,6dibromopyridine (4 eq.) in the presence of Pd(PPh3)4 (10%) and K2CO3 (2N) in Toluene/EtOH/water.…”

Entwined dimer formation from self-complementary bis-acridiniums

“…Remarkably, this spectrum exhibits similar chemical shifts than our previously reported Triphenyl-bis-acridinium receptor which was in a fast exchange regime at 5•10 -4 mol•L -1 . 13 More especially, the chemical shifts of the acridinium protons ((H1/8) = 8.13, (H2/7) = 7.86, (H3/6) = 8.41 and (H4/5) = 8.64 ppm) are similar for both molecules (see ESI,). This observation suggests that the acridinium protons are not affected by the difference in the electronic environment of the spacer and experienced a solvated environment close to the isolated monomer of 1•2PF6.…”

“…using n-BuLi (1 eq.) in hexanes (2.5 mol•L -1 ), then followed by addition of 10-methyl-9(10H)acridone 13 at -78°C (1 eq.) led to the corresponding hydroxyacridane intermediate.…”