Modulating luminescence spectra by controlling the π∙∙∙π stacking strength of the excimers of a new europium complex material

Chai, Wenxiang; Zhang, Xiaoli; Song, Li; Hong, M.; Shi, He; Wang, Congyong; Guo, Jiayu; Zheng, Xijuan; Chen, Gang; Shu, Kangying

doi:10.1016/j.matlet.2015.01.055

Cited by 17 publications

(4 citation statements)

References 20 publications

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“…It is known that photoluminescence (PL) measurements may prove the existence of 𝜋-𝜋 stackings by excimer formation. [36,37] Unfortunately, our materials were PL inactive, so we could not proceed with the measurement. However, when we measured the Fourier transform infrared (FT-IR) spectra of Pht-bNC gels, we were able to observe that the C=O stretching peak shifted from 1722 to 1716 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Kim

Lee

Bae

et al. 2022

Macromol. Rapid Commun.

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The design and synthesis of phthalimide derivatives are important goals for applications in fields such as pharmaceutical science and optoelectronics. In the present study, a facile and convenient synthetic pathway (no heat or acid/catalyst needed) is devised to produce phthalimides from a biomass-derived furan by directly introducing an N-carbamate group at the C-2 position of the furan ring via thermal Curtius rearrangement. The electron-donating N-carbamate group increases the energy level of the highest occupied molecular orbital of the furan diene, resulting in a significant increase of the rate of the Diels-Alder reaction with maleimide compared to the conventional furfuryl furan. Interestingly, the Diels-Alder adduct smoothly undergoes aromatization (dehydration) to generate the phthalimide motif. It is shown that the biomass-derived phthalimides can produce supramolecular gels and act as sensors of basic anions like F − and CN − . The novel synthetic pathway to phthalimide derivatives from a biomass-derived furan can potentially be used to develop novel phthalimide motifs for a variety of applications.

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Section: Resultsmentioning

confidence: 99%

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Kim

Lee

Bae

et al. 2022

Macromol. Rapid Commun.

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“…All the reagents, except the diimine ligand of 2‐PBO, were purchased and used without further purification. This N^N‐type ligand was synthesized by a condensation reaction of pyridyl‐2‐carboxylate with ortho‐aminophenol using a modified procedure 7c, 18 . Thin films (5% wt) of polymethyl methacrylate (PMMA)–cuprous complex were prepared by dissolving the compound in dichloromethane and then spin‐coating using a quartz plate.…”

Section: Methodsmentioning

confidence: 99%

Heteroleptic [Cu(NN)P₂]⁺‐type cuprous complexes and their structural modulation on phosphorescent color: Synthesis, structural characterization, properties, and theoretical calculations

Wang

Song

Wang

et al. 2020

Applied Organom Chemis

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Four new heteroleptic [Cu(NN)P2]+‐type cuprous complexes—1‐TPP, 2‐POP, 3‐Xantphos, and 4‐DPPF—were designed and synthesized using a diimine ligand 2‐(2′‐pyridyl)benzoxazole (2‐PBO) and different phosphine ligands (TPP, triphenylphosphine; POP, bis[2‐(diphenylphosphino)phenyl]ether; Xantphos, 4,5‐bis(diphenylphosphino)‐9,9‐dimethylxanthene; DPPF, 1,1′‐bis(diphenylphosphino)‐ferrocene). All complexes were characterized using single‐crystal X‐ray diffraction, spectroscopic analysis (infrared, UV–Vis.), elemental analysis, and photoluminescence (PL). Single‐crystal X‐ray diffraction revealed complexes 1–4 as isolated cation complex structures with a tetrahedral CuN2P2 coordination geometry and diverse P–Cu–P angles. Their UV–Vis. absorption spectra exhibited a blue‐shift sequence in wavelength with an enlarged P–Cu–P angle from 4 to 2 then to 3 and then to 1. The PL emission peaks of 1–3 also exhibited a similar blue‐shift sequence (2 → 3 → 1). Their PL lifetime in microseconds (~7.5, 5.1, and 4.7 μs for 1, 2, and 3, respectively) indicated that their PL behavior represents phosphorescence. Time‐dependent density functional theory (TD‐DFT) calculation and wavefunction analysis revealed that S1 and T1 states of 1–3 should be assigned as metal–ligand and ligand–ligand charge‐transfer (ML + L'L)CT states. Their UV–Vis. absorption and phosphorescence should be attributed to the charge transfer from the P–Cu–P segment to the 2‐PBO ligand. Therefore, as the P–Cu–P angle increased (lower HOMO), the energy of S1 and T1 states also increased, following the change of PL color.

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“…The C-H� � �� interaction involves the C13-H13 group and the C6-C11 ring, and the C� � ��(centroid) and H� � ��(centroid) distances are 3.515 (3) and 2.6475 (11) A ˚, respectively. In addition, there is a strong �-� stacking interaction between two adjacent complex cations (Hong et al, 2014;Chai et al, 2015b;Tao et al, 2018;Wang et al, 2020a), thus forming a supramolecular dimer structure (Fig. 3).…”

Section: Figurementioning

confidence: 99%

“…type complexes, the low-energy transition (typically around 400 nm) should be assigned to the charge transfer mechanism, usually the metal-to-ligand charge transfer (MLCT) mechanism or the ligand-to-ligand charge transfer (LLCT) mechanism, or a combination of both (Chai et al, 2015a;Zhao et al, 2016;Tao et al, 2018;Wang et al, 2020a). The other highenergy band usually appears at �300 nm, which should be assigned as a �-�* transition within a ligand (Hong et al, 2014;Zhang et al, 2014;Chai et al, 2015b). However, for complex I, there should be three transition modes corresponding to the three absorption bands.…”

Section: Figurementioning

confidence: 99%

Structural, spectroscopic, luminescence sensing and TD–DFT theoretical studies of a CuP₂N-type complex

Zhang

et al. 2023

Acta Crystallogr C

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Luminescent cuprous complexes are an important class of coordination compounds due to their relative abundance, low cost and ability to display excellent luminescence. The title heteroleptic cuprous complex, [2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl-κ2 P,P′](2-phenylpyridine-κN)copper(I) hexafluoridophosphate, rac-[Cu(C44H32P2)(C11H9N)]PF6, conventionally abbreviated rac-[Cu(BINAP)(2-PhPy)]PF6 (I), where BINAP and 2-PhPy represent 2,2′-bis(diphenylphosphanyl)-1,1′-binaphthyl and 2-phenylpyridine, respectively, is described. In this complex, the asymmetric unit consists of a hexafluoridophosphate anion and a heteroleptic cuprous complex cation, in which the cuprous centre in a CuP2N coordination triangle is coordinated by two P atoms from the BINAP ligand and by one N atom from the 2-PhPy ligand. Time-dependent density functional theory (TD–DFT) calculations show that the UV–Vis absorption of I should be attributed to ligand-to-ligand charge transfer (LLCT) characteristic excited states. It was also found that the paper-based film of this complex exhibited obvious luminescence light-up sensing for pyridine.

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Modulating luminescence spectra by controlling the π∙∙∙π stacking strength of the excimers of a new europium complex material

Cited by 17 publications

References 20 publications

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Heteroleptic [Cu(NN)P₂]⁺‐type cuprous complexes and their structural modulation on phosphorescent color: Synthesis, structural characterization, properties, and theoretical calculations

Structural, spectroscopic, luminescence sensing and TD–DFT theoretical studies of a CuP₂N-type complex

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Modulating luminescence spectra by controlling the π∙∙∙π stacking strength of the excimers of a new europium complex material

Cited by 17 publications

References 20 publications

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Supramolecular Phthalimide Networks Via Tandem Diels–Alder Reaction–Aromatization Using Biomass‐Derived Furanic Dienes

Heteroleptic [Cu(NN)P2]+‐type cuprous complexes and their structural modulation on phosphorescent color: Synthesis, structural characterization, properties, and theoretical calculations

Structural, spectroscopic, luminescence sensing and TD–DFT theoretical studies of a CuP2N-type complex

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Product

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Heteroleptic [Cu(NN)P₂]⁺‐type cuprous complexes and their structural modulation on phosphorescent color: Synthesis, structural characterization, properties, and theoretical calculations

Structural, spectroscopic, luminescence sensing and TD–DFT theoretical studies of a CuP₂N-type complex