AIEgens-NLOphores coumarin-triphenylamine chalcone derivatives: Synthesis, photophysical properties and DFT computational study

Blanco-Acuña, Edgard Fabián; Vázquez-López, Luis Antonio; Gasque, Laura; García-Ortega, Héctor

doi:10.1016/j.molstruc.2022.134009

Cited by 10 publications

(2 citation statements)

References 110 publications

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“…4,5 The basic strategy of including electron donor and acceptor substituents to polarize the p-electron system of organic materials has been employed in the development of NLO chromophores with high rst and second order hyperpolarizabilities, good thermal stability, improved solubility and processability. 8,10 In addition to what was previously mentioned, chalcones with biologically relevant groups such as quinolines or 1,3benzodioxol derivatives stand out for their wide variety of biological properties, such as antioxidants, antimicrobials, anticancer, anti-inammatory, among others. [11][12][13][14][15][16][17] These properties, together with their intrinsic NLO properties, make chalcones especially interesting for the design of optical materials with biomedical applications.…”

Section: Introductionmentioning

confidence: 99%

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Nonlinear optical and spectroscopic properties, thermal analysis, and hemolytic capacity evaluation of quinoline-1,3-benzodioxole chalcone

Polo-Cuadrado,

Osorio,

Acosta-Quiroga

et al. 2024

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

“…The basic strategy of including electron donor and acceptor substituents to polarize the π-electron system of organic materials has been employed in the development of NLO chromophores with high first and second order hyperpolarizabilities, good thermal stability, improved solubility and processability. 8,10…”

Section: Introductionmentioning

confidence: 99%

Nonlinear optical and spectroscopic properties, thermal analysis, and hemolytic capacity evaluation of quinoline-1,3-benzodioxole chalcone

Polo-Cuadrado,

Osorio,

Acosta-Quiroga

et al. 2024

RSC Adv.

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Unravelling the Optoelectronic and Biological Properties of Phenanthroimidazo [1,2‐c] Quinazoline‐Based Donor‐Acceptor Materials

Ganesan,

Ranganathan,

Vijay Solomon

et al. 2024

Asian J Org Chem

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Imidazo[1,2‐c]quinazoline is widely established as biologically spectral active materials, while their optoelectronic properties were seldom investigated in the literature. In this context, this research work introduced two donors of varying strength, such as triphenylamine (TP) and phenothiazine (PZ) units, into the phenanthroimidazo [1,2‐c] quinazoline acceptor unit to form donor‐acceptor type luminescence materials such as TPQZ and PZQZ, respectively and were characterized by NMR and mass spectroscopy. Both these materials exhibited intramolecular charge transfer (ICT) type absorption (∼380−450 nm) and emission (∼540−600 nm) characteristics, which attributed to the electronic transition occurring from the HOMO of the PZ/TP donor to the LUMO+1 and LUMO+2 of the imidazo [1,2‐c] quinazoline acceptor unit, as predicted using DFT calculations. Increasing the electron donor strength was not only limited to fine‐tuning the π→π* based localized (∼400−450 nm) to ICT (∼450−650 nm) emission characteristics in both the solution and solid‐state conditions but also found to improve the zone of inhibition to 16 mm against Staphylococcus aureus/Bacillus subtilis bacterial species. The scope of realizing the luminescence nature of this acceptor unit is further expanded towards tagging biological samples such as E. coli. This work opens up a new paradigm in developing luminescent materials for optoelectronic and biological applications.

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Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

Liu,

Yao,

et al. 2024

Eur J Org Chem

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Two analogues of rofecoxib, 2‐Pyr‐ROF and 2‐Pip‐ROF, were designed according to the strategy of heterocyclic ring enlargement and facilely synthesized in a facile manner by Knoevenagel reactions. The first compound, 2‐Pyr‐ROF, had low quantum yields (QY) of 3.0% in the solid states. After replacing the pyrrolidinyl with piperidinyl, the resulting 2‐Pip‐ROF had a significantly increased QY, with a value of 28%. The root‐mean‐square deviation (RMSD) values between S0 and S1 of 2‐Pyr‐ROF and 2‐Pip‐ROF in tetrahydrofuran were 0.51, 0.35 Å, respectively. As compared with 2‐Pyr‐ROF, compound 2‐Pip‐ROF exhibits a smaller RMSD, which indicates a lower non‐radiative transition rate. A single‐crystal X‐ray diffraction study and Hirshfeld surfaces analysis revealed that 2‐Pip‐ROF had a more nonplanar molecule structure and a weaker π‐π interaction, which might result in a higher fluorescence intensity and QY. Owing to its better aggregation‐induced emission (AIE) behavior, compound 2‐Pip‐ROF showed more multi‐functional applications, including mechanochromism, acidochromism, and lipid droplets imaging ability. These results imply that the strategy of heterocyclic ring enlargement provides a new paradigm for the design of new luminogens with AIE properties.

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AIEgens-NLOphores coumarin-triphenylamine chalcone derivatives: Synthesis, photophysical properties and DFT computational study

Cited by 10 publications

References 110 publications

Nonlinear optical and spectroscopic properties, thermal analysis, and hemolytic capacity evaluation of quinoline-1,3-benzodioxole chalcone

Nonlinear optical and spectroscopic properties, thermal analysis, and hemolytic capacity evaluation of quinoline-1,3-benzodioxole chalcone

Unravelling the Optoelectronic and Biological Properties of Phenanthroimidazo [1,2‐c] Quinazoline‐Based Donor‐Acceptor Materials

Effects of a Larger N‐Heterocyclic Ring in Rofecoxib Analogues on AIE Activity and Multifunctional Applications

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