AIEE active J-aggregates of naphthalimide based fluorescent probe for detection of Nitrobenzene: Combined experimental and theoretical approaches for Non-covalent interaction analysis

• Published in: Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy Vol. 290; p. 122273
• Main Authors: Khadija, Irshad, Hasher, Rafique, Sanwa, Khan, Asad Muhammad, Nawazish, Shamyla, Rehman, Habib ur, Imran, Muhammad, Shahzad, Sohail Anjum, Farooq, Umar
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 05.04.2023; Elsevier BV
• Subjects: AIEE, J-aggregates; Nitrobenzene; Non-covalent interaction; PET; AIEE, J-aggregates; Nitrobenzene; Non-covalent interaction; PET
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2022.122273

[Display omitted] •A new 1,8-naphthalimide based fluorescent probe NS was synthesized by single step imidation reaction.•Probe NS displayed AIEE characteristics with remarkable red-shifted J-aggregates.•Sensing of NB was attributed to J-aggregates formation of probe NS.•Probe exhibited highly selective fluorometric detection of nitrobenzene (NB) down to nanomolar level. A new naphthalimide-based fluorescent probe NS with exceptional J-aggregates based aggregation-induced emission enhancement (AIEE) properties was rationally synthesized through a single-step imidation reaction. Probe NS exhibited excellent AIEE properties in aqueous media through the formation of J-aggregates with remarkable red-shift. The AIEE active probe NS was used for selective and sensitive detection of nitrobenzene (NB) based on fluorescence quenching response. Formation of J-aggregates was assessed through fluorescence titration. These J-aggregates contributed significantly to produce favorable interaction between probe NS and NB. The highly selective fluorescence detection of NB was accredited to the adjustable smaller size of NB that can easily penetrate into interstitial spaces of probe molecules. Ability of sensor to detect NB in solid state was also accomplished through solid state fluorescence spectroscopy. Nature of interaction and sensitivity of probe NS for NB has also been investigated through 1H NMR titration and density functional theory (DFT) including non-covalent interaction (NCI), quantum theory of atom in molecule (QTAIM), electron density differences (EDD), frontier molecular orbitals (FMO) and density of states (DOS) analysis. Advantageously, probe exhibited colorimetric and vapor phase detection of NB. Moreover, probe was quite sensitive for the trace detection of NB in real samples.