PET fluoroionophores for Zn2+ and Cu2+: complexation and fluorescence behavior of anthracene derivatives having diethylamine, N-methylpiperazine and N,N-bis(2-picolyl)amine units

Abstract

Anthracene derivatives (1, 2) having one or two diethylamine (a), N-methyl-piperazine (b) and N,N-bis(2-dipicolyl)amine units (c) showed weak emission, suggesting that photoinduced electron transfer (PET) from the amine group to the excited anthracene occurs. The PET fluoroionophores (1, 2) were found to display unique photophysical properties in the presence of the guest metal salts. Complexation of diethylamine (1a, 2a) and N-methyl-piperazine derivatives (1b, 2b) with Ni 2+ , Cu 2+ and Zn 2+ enhanced the emission, while the emission intensities of N,N-bis(2picolyl)amine derivatives (1c, 2c) are increased in the presence of Zn 2+ and decreased in the presence of Ni 2+ and Cu 2+ . The crystal structures of 2c and its zinc chloride complex showed that the binding of Zn 2+ to the N,N-bis(2-picolyl)aminomethyl unit inhibits the photoinduced electron transfer process. Intramolecular p-p interactions between anthracene and the ZnCl 2 -complexed pyridine were observed.

New fluorescent pH sensors based on covalently linkable PET rhodamines

“…Here we present a new class of amino-functional rhodamines the pH-sensitivity of which originates from the intramolecular photoinduced electron transfer process (PET, [37–42] ) between non-protonated amino groups and the excited chromophore ( Fig. 1 ).…”

Crystal Structure and Complexation and Fluorescence Behaviors of 1,4-Bis (9-anthracenylmethyl) piperazine

“…De Silva et al 1,4,6 have created a photoinduced electron transfer PET fl uoroionophore consisting of an azacrown ether with an anthryl group. We have reported that multi-donor-spacer-multi-acceptor systems [7][8][9][10][11][12][13] such as diaza-18-crown-6 1 and diaza-12-crown-4 2 ethers, carrying two 9-anthrylmethyl groups, have a higher fluorescence switch-on ability for guest cation complexation than those of the corresponding monoazacrown derivatives Scheme 1 . Piperazine is widely used as a chelate.…”

Synthesis of AB‐type block copolymers containing benzoxazole and anthracene groups by ATRP and fluorescent property

“…A series of 2‐(stilben‐4‐yl)benzoxazole derivatives prepared by Andrzej et al was used as a dopant in the fabrication of organic light‐emitting diodes 15. Moreover, the anthracene group with rigid large π‐conjugated structure is generally used as matrix for synthesizing all sorts of optical compounds 16–19…”