RESUMO
In this paper, the synthesis of a naphthalene diimide (NDI) derivative with a donor-acceptor-donor (D-A-D) molecular structure substituted with a long alkyl chain (12 carbons) containing naphthalene hydrazide at the imide position is reported. The reduced emission quantum yield (φf = 0.01-0.03) of the NDI derivative in various solvents indicates the perturbation of the electronic state of π-electron deficient NDI (A) by the peripheral naphthalene (D) units. The investigation of the influence of the alkyl chain and naphthalene substituent on the self-assembling properties of the NDI derivative reveals an isodesmic mode of self-assembly in a chloroform/methylcyclohexane (CHCl3/MCH, 1 : 9, v/v) mixture. The self-assembling nature of the NDI derivative also results in the formation of an organogel in the CHCl3/MCH (1 : 9, v/v) mixture, and gel formation is well-comprehended by techniques such as P-XRD, rheological studies, and FT-IR measurements. Furthermore, radical anion (NDIË-) formation of π-acidic NDI was used as a sensing tool for hydrazine by a fluorescence "turn-on" (φf = 0.12) method in the solution (DMSO), film, and gel state with a detection limit of 284.1 ppb in DMSO and 32 ppb in the gel state.
RESUMO
A squaramide ring conjugated with Schiff-bases decorated with hydroxy and methoxy functional groups differentially senses zinc and cadmium ions, which turn on the fluorescence. The feebly emitting free ligands light up in the presence of zinc and cadmium acetates, with the acetate ion playing a pivotal role as a conjugate anion. The selective and differentiable emission responses for zinc and cadmium ions make these ligands efficient multi-analyte sensing agents. Furthermore, these ligands could be used to differentially sense zinc and cadmium ions even in aqueous environments. The NMR investigations reveal marginal differences in the binding of zinc and cadmium ions to the ligands, whereas density functional theory calculations suggest the different extent of ligand-to-metal charge transfer (LMCT) contributes to the differential behavior. Finally, comparison of the excited-state dynamics of free ligand and the metal complexes reveal the appearance of longer lifetime (about 500-700â ps) component with complexation, due to rigidified molecular skeleton, thereby impeding the non-radiative processes.
RESUMO
Perylene diimide (PDI) derivatives exhibit a high propensity for aggregation, which causes the aggregation-induced quenching of emission from the system. Host-guest chemistry is one of the best-known methods for preventing aggregation through the encapsulation of guest molecules. Herein we report the use of 18-crown-6 (18-C-6) as a host system to disaggregate suitably substituted PDI derivatives in methanol. 18-C-6 formed complexes with amino-substituted PDIs in methanol, which led to disaggregation and enhanced emission from the systems. Furthermore, the embedding of the PDIâ 18-C-6 complexes in poly(vinyl alcohol) (PVA) films generated remarkably high emission quantum yields (60-70 %) from the PDI derivatives. More importantly, the host-guest systems were tested for their ability to conduct electricity in PVA films. The electrical conductivities of the self-assembled systems in PVA were measured by electrochemical impedance spectroscopy (EIS) and the highest conductivity observed was 2.42×10(-5) â S cm(-1) .