Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Abstract

N-(aminoalkyl)-4-chloronaphthalene-1,8-dicarboximides 1, N-(aminoalkyl)-4-acetamidonaphthalene-1,8-dicarboximides 3 and N,N'-bis(aminoalkyl)-perylene-3,4:9,10-tetracarboxydiimides 4 show good fluorescent off ± on switching in aqueous alcoholic solution with protons as required for fluorescent PET sensor design. The excitation wavelengths lie in the ultraviolet (l max 345 and 351 nm) for 1 and 3 and in the blue-green (l max 528, 492 and 461 nm) for 4; the emission wavelengths lie in the violet (l max 408 nm) for 1, in the blue (l max 474 nm) for 3 and in the yellow-orange (l max 543 and 583 nm) for 4. Compound 4 b shows substantial fluorescence enhancement with protons when immobilized in a poly(vinylchloride) matrix, provided that 2-nitrophenyloctyl ether plasticizer and potassium tetrakis(4-chlorophenyl)borate additive are present to prevent dye crystallization and to facilitate proton diffusion into the membrane, respectively.

Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer

“…Analysis of these absorbance (A) changes according to Eq. (2) [12] gives the pK a values 3.1 and 1.9, respectively.…”

New Thermotropic Dyes Based on Amino-Substituted Perylendicarboximides

“…They have received considerable attention on account of their use as antitumor agents, [15] fluorescent cell markers and stains, [16] laser dyes, [17] dyes for synthetic polymers, [18] solar collectors, [19] fluorescent flaw detectors, [20] models for PET processes, [21] electroluminescent devices, [22] and very recently as fluorescent pH sensors. [23] However, 9-amino-N-(2,6-diisopropylphenyl)perylene-3,4-dicarboximide seems an especially promising starting material for further synthetic dye chemistry, for example, the preparation of new azo dyes.…”

Supramolecular Assembly of Perylene Bisimide with β‐Cyclodextrin Grafts as a Solid‐State Fluorescence Sensor for Vapor Detection

“…The higher sensitivity to aniline is attributed to photoinduced electron transfer from the reducing reagents to the excited states of chromophores. [24] …”