A novel 1,8-naphthalimide derivative with an open space for an anion: unique fluorescence behaviour depending on the binding anion's electrophilic properties

Abstract

We have designed a novel 1,8-naphthalimide derivative with an open space for an anion. Computational calculation has predicted that the space could trap various anion species and photo-induced charge transfer depending on the anion's electrophilic properties. Indeed, the fluorescence behaviour of the 1,8-naphthalimide derivative complexes with each anion is consistent with the computational prediction.

Strong and Reversible Circularly Polarized Luminescence Emission of a Chiral 1,8‐Naphthalimide Fluorophore Induced by Excimer Emission and Orderly Aggregation

“…As predicted, R , R / S , S ‐ 2 have two fluorescent emission peaks when excited at 330 nm. One is a monomer emission peak at around 382 nm due to the 1,8‐naphthalimide groups and the other is broad peak at around 482 nm, which can be regarded as an excimer emission from the 1,8‐naphthalimide groups . Upon the addition of water, R , R / S , S ‐ 2 initially showed polarity‐induced fluorescence enhancement in THF/H 2 O mixtures .…”

“…One is am onomer emission peak at around3 82 nm due to the 1,8-naphthalimide groups and the other is broad peak at around4 82 nm, which can be regarded as an excimer emission from the 1,8-naphthalimide groups. [9] Upon the addition of water, R,R/S,S-2 initially showed polarity-induced fluorescencee nhancement in THF/H 2 Om ixtures. [10] However,w hen the water fraction was over 80 %, the emission intensity of R,R/ S,S-2 exhibits af luorescence quenching response behavior with a6 2nmb athochromic shift for the monomer emission peak at a9 5% water fraction.Thisc an be attributedt ot he aggregation formation of the 1,8-naphthalimide groups.…”

Imidazolium Based Probes for Recognition of Biologically and Medically Relevant Anions

“…Izawa, Sumita and co‐workers have designed a 1,8‐naphthalimide derivative 2 with an open space for encapsulation of anions because of electrostatic interaction with the imidazolium ion and an anion‐π interaction with 1,8‐naphthalimide moiety. On excitation at 360 nm, derivative 2 showed emission at 400 and 480 nm, respectively corresponding to monomer and excimer emission bands of 1,8‐naphthalimide.…”

Machine Learning Analysis for Photo-Induced Phenomena of 1-Methyl-3-(N-(1,8- Naphthalimidyl)ethyl)imidazolium Salts

“…Conventional experimental and computational approaches show that complex chemical phenomena, such as non-adiabatic transition and excimer formation, are involved in the photoinduced process of MNEI complexes. [1][2][3][4] Hence, much time is required to detect and identify the physical characteristics that allow MNEI to act as an anion sensor. Furthermore, because the number of experimentally available MNEI salt is only a degree of countable, predicting the properties of unidentified chemical compounds is impossible.…”