Highly fluorescent blue-green emitting phenanthroimidazole derivatives: Detail experimental and DFT study of structural and donating group effects on fluorescence properties

Kothavale, Shantaram; Bhalekar, Sulochana; Sekar, Nagaiyan

doi:10.1016/j.dyepig.2018.06.020

Cited by 20 publications

(25 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Section: Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

“…Kothavale et al designed different ESIPT-reactive phenanthro [9,10-d]imidazoles bearing different electron-donating groups and an extended phenyl group at the anthracene moiety, as described in Scheme 10. 200 The extended conjugation network and rigidity associated with the donor−acceptor structure are usually related to the modification of photophysical properties. Indeed, red-shifted absorption, emission peaks, and improved quantum yields were observed in different organic solvents.…”

Section: ■ Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

See 1 more Smart Citation

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

et al. 2022

View full text Add to dashboard Cite

Fluorescent and colorimetric sensors are important tools for investigating the chemical compositions of different matrices, including foods, environmental samples, and water. The high sensitivity, low interference, and low detection limits of these sensors have inspired scientists to investigate this class of sensing molecules for ion and molecule detection. Several examples of fluorescent and colorimetric sensors have been described in the literature; this Review focuses particularly on phenanthro [9,10d]imidazoles. Different strategies have been developed for obtaining phenanthro [9,10d]imidazoles, which enable modification of their optical properties upon interaction with specific analytes. These sensing responses usually involve changes in the fluorescence intensity and/or color arising from processes like photoinduced electron transfer, intramolecular charge transfer, intramolecular proton transfer in the excited state, and Forster resonance energy transfer. In this Review, we categorized these sensors into two different groups: those bearing formyl groups and their derivatives and those based on other molecular groups. The different optical responses of phenanthro [9,10-d]imidazole-based sensors upon interaction with specific analytes are discussed.

show abstract

Section: Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

Section: ■ Fluorescent Imidazole Sensor Based On Esipt Processmentioning

confidence: 99%

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Effect of solvent polarity using polarity plots give idea about how solvents dielectric constant and refractive index affects compounds but it does not consider other solvent factors such as "solvent acidity", "solvent basicity", "solvent polarizability" or "solvent dipolarity", and hence MLR analysis is used to find the influence of solute-solvent polarity, polarizability, acidity and basicity of solvents. [60][61][62][63] We have done the MLR study usingboth "Kamlet Taft" and "Catalan parameters" in which "Catalan" parameters give comparatively better values of regression constant than the "Kamlet" parameters. There is no much difference in absorption values but emission and Stokes shift values show negative estimated coefficients.…”

Section: Multilinear Regression Analysis (Mlr) By Kamlet Taft and Catmentioning

confidence: 99%

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

2019

Self Cite

View full text Add to dashboard Cite

Three novel hydroxyl substituted and triphenylamine sidearm coumarin decorated molecules were prepared to examine the effect of adjacent hydroxyl substituent as well as coumarin units on the photophysical linear and nonlinear optical properties. Both hydroxyl function adjacent to the phenyl ring and extra coumarin unit is attributed to the red shifted absorption (435‐487 nm) and emission (496‐578 nm) compared to the plain triphenylamine based coumarin derivatives. Positive solvatochromism around 70 nm was observed in solvents with different polarity polarities and it is reinforced by solvent polarity plots and multilinear regression study. Very high viscosity induced emission enhancement (5.7 – 8.2 fold) was observed for in ethanol/polyethylene glycol‐400 system, highlighting their capability to act as efficient fluorescent molecular rotors (FMRs). The nonlinear optical properties were investigated by solvatochromism as well as a computational method using B3LYP 6–311++G (d, p) basis set. All these compounds exhibited large magnitudes of first order (65‐208x10 −30e.s.u) and second order (560‐2120x10 −36e.s.u) hyperpolarizability.

show abstract

“…Small-molecule organic fluorophores, due to their ease of synthesis, tunable photophysical properties, and good thermal stability, have found extensive applications in electroluminescence, chemical sensing, and bioimaging. − Among the vast array of organic fluorophores reported in the literature, phenanthrene-based molecular systems have attracted considerable attention in recent years because of their appealing luminescent properties, such as versatile liquid and solid-state fluorescence, long emission lifetimes, and high quantum yields. − 1 H -Phenanthro[9,10- d ]imidazole (herein referred to as PI , Figure ) is a heterocyclic derivative of phenanthrene in which a 1,3-imidazole ring is fused with the 9,10 C–C bond of phenanthrene. As such, the PI molecule possesses a planar π-delocalized framework that gives rise to rich (opto)electronic activities.…”

Section: Introductionmentioning

confidence: 99%

Donor–Acceptor Fluorophores and Macrocycles Built Upon Wedge-Shaped π-Extended Phenanthroimidazoles

Abdollahi

Zhao

2023

J. Org. Chem.

View full text Add to dashboard Cite

A class of wedge-shaped organic π-fluorophores featuring a 6,9-diphenyl-substituted phenanthroimidazole (PI) core was designed, synthesized, and characterized. Among them, a π-extended PI derivative containing two electron-withdrawing aldehyde groups was found to exhibit versatile solid-state packing properties as well as strong solvatofluorochromism in different organic solvents. Another PI derivative that was functionalized with two electron-donating 1,4-dithiafulvenyl (DTF) end groups showed versatile redox reactivities and quenched fluorescence. Treatment of this wedge-shaped bis(DTF)-PI compound with iodine resulted in oxidative coupling reactions, leading to the formation of intriguing macrocyclic products that carry redox-active tetrathiafulvalene vinylogue (TTFV) moieties in their structures. Mixing the bis(DTF)-PI derivative with fullerene (C60 or C70) in an organic solvent resulted in substantial fluorescence enhancement (turn-on). In this process, fullerene acted as a photosensitizer to generate singlet oxygen, which in turn induced oxidative C = C bond cleavages and converted nonfluorescent bis(DTF)-PI into highly fluorescent dialdehyde-substituted PI. Treatment of TTFV–PI macrocycles with a small amount of fullerene also led to a moderate degree of fluorescence enhancement, but this is not because of photosensitized oxidative cleavage reactions. Instead, competitive photoinduced electron transfer from TTFV to fullerene can be attributed to their fluorescence turn-on behavior.

show abstract

Highly fluorescent blue-green emitting phenanthroimidazole derivatives: Detail experimental and DFT study of structural and donating group effects on fluorescence properties

Cited by 20 publications

References 47 publications

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

Aryl-Phenanthro[9,10-d]imidazole: A Versatile Scaffold for the Design of Optical-Based Sensors

Coumarin and Hydroxyl Decorated Viscosity Sensitive Triphenylamine Derivatives: Synthesis, Photophysical Properties, Viscosity Sensitivity, TD‐DFT, and NLO Properties

Donor–Acceptor Fluorophores and Macrocycles Built Upon Wedge-Shaped π-Extended Phenanthroimidazoles

Contact Info

Product

Resources

About