Novel A–π–D–π–A type molecules based on diphenylamine and carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property

Wang, Yingyi; Lai, Guoqiao; Li, Zhifang; Ma, Yuguang; Shen, Yongjia; Wang, Chengyun

doi:10.1016/j.tet.2015.03.003

Cited by 18 publications

(11 citation statements)

References 50 publications

(1 reference statement)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An increase in the solvent polarity from THF to DMSO revealed positive solvatochromism of the absorption spectra of the β‐ketoimines with a redshift of λ max of 51 ( L1 ), 61 ( L2 ), 52 ( L3 ), and 37 ( L4) nm (see Figures S47–S50), which indicates that polar solvents can lead to better stabilization of a polarized excited state, arising from extended intramolecular charge transfer (ICT) from the ferrocenyl donor to the acceptor moieties [56] . The redshift of the λ max values with increasing solvent polarity reveals an increase in the dipole moment upon excitation, in agreement with the results of TD‐DFT calculations (Table 2), which predicted that the excited states of these β‐ketoimines should be more polar than the ground states [57] …”

Section: Resultssupporting

confidence: 81%

See 1 more Smart Citation

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

David

Colombo

Dragonetti

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

As eries of new b-ketoimines containing af errocene moiety and their BF 2 complexes have been synthesized and structurally characterized. The solvatochromism of the b-ketoimines was studied, putting in evidencearedshift with increasing solvent polarity.T his positive solvatochromism can be attributed to am ore polarizede xcited state compared with the grounds tate, due to intramolecular charge transfer( ICT) transitions. The b-ketoimines exhibited weak emission, attributable to the excited-state intramolecular proton transfer( ESIPT) phenomenon. This ESIPT effect is suppressedu ponr estriction of the keto-enaminet automerism, inducedu pon addition of BF 3 •OEt 2 ,w hich afforded the related BF 2 complexes, characterized by an enhancement of the fluorescence through the ICT effect. Both the b-ketoimines and BF 2 complexes exhibited significant aggregation-inducede mission behavior in mixtureso fC H 3 CN/H 2 O, due to restriction of intramolecular rotationint he aggregated state. The frontier molecular orbital levels,g round-and excitedstate dipole moments (m g and m e ), and the origin of electronic absorption spectra were studied by time-dependent DFT calculations. The second-order nonlinearo ptical (NLO) properties were determined by the electric-field-induced secondharmonic generation technique. The mb 1907 values of the bketoimines increased upon the formationo ft he related BF 2 complexes,m ainly due to an enhancement of the groundstate dipole moment. The resultsp resented here reveal that some of these novel compounds are excellent multifunctional candidates for NLO and luminescence applications.

show abstract

Section: Resultssupporting

confidence: 81%

“…[56] The redshift of the l max values with increasing solvent polarity reveals an increase in the dipole moment upon excitation,i na greement with the results of TD-DFT calculations (Table 2), which predicted that the excited states of these b-ketoimines should be more polar than the ground states. [57]…”

Section: Solvatochromismmentioning

confidence: 99%

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

David

Colombo

Dragonetti

et al. 2021

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…In comparison with the solution without added water, the intensity was increased by 44‐fold for L1 and 55‐fold for L2 at 95% fraction of water as shown in Figure . Therefore, according to the similar work in literature, these types of compounds that have the properties mentioned above show AIE characteristics …”

Section: Resultsmentioning

confidence: 71%

“…Therefore, according to the similar work in literature, these types of compounds that have the properties mentioned above show AIE characteristics. 23,35,40,53,54…”

Section: Synthesis and Aie Properties Of New Chiral Thiazole Derivamentioning

confidence: 99%

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Halay

Bozkurt

2017

Chirality

View full text Add to dashboard Cite

Hydrogen bonding and π-π interactions take special part in the enantioselectivity task. In this regard, because of having both hydrogen acceptor and hydrogen donor groups, melamine derivatives become more of an issue for enantioselectivity. In the light of such information, triazine-based chiral, fluorescence active novel thiazole derivatives L1 and L2 were designed and synthesized from (S)-(-)-2-amino-1-butanol and (1S,2R)-(+)-2-amino-1,2-diphenylethanol. The structural establishment of these compounds was made by spectroscopic methods such as FTIR, H, and C NMR. While the solution of these compounds in DMSO did not show any fluorescence emission, it was observed that the emission increased 44-fold for L1 and 55-fold for L2 in 95% water, similar to the aggregation-induced emission (AIE) characterized compounds. In this regard, enantioselective capabilities of these compounds against carboxylic acids were tested, and in experiments carried out at a ratio of 40/60 DMSO/H O, it was determined that R-2ClMA increased the fluorescence emission of L1 chiral receptor by 2.59 times compared to S-isomer.

show abstract

“…The targeted dyes giving emissive blue (B1), [42] green (G2), [43] yellow (Y3) [44] and red (R4) [45] materials in the solid state were selected based on the carbazole (B1, Y3, R4) and benzofuran (G2) units (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Refined RGB Strategy for the Synthesis of Polymer‐Based Full Organic Luminescent Nanotubes with Broad Emission Bands

et al. 2020

View full text Add to dashboard Cite

Light-emitting polymer nanotubes with tailored fluorescence emission bands have been prepared using organic emissive materials based on benzofuran, carbazole, and indolocarbazole scaffolds and investigated with the goal to obtain pure whitelight emission at the nanoscale. The polymer nanostructures were obtained by the anodic aluminium oxide (AAO) template method with PMMA as a transparent polymer matrix and a proficient choice of organic dyes emitting in the blue, green, yellow and red parts of the spectral range. It is demonstrated that combining aqueous dispersions of monochromatic nanotubes is an effective way of generating white light emission due to a simple correlation between the individual color components. Furthermore, it is also possible to target white emission at the nanoscale by adjusting the concentration of the dyes inside single nanotubes in order to obtain optimal color coordinates of ca. 0.3 in the CIE chromaticity diagram.

show abstract

Novel A–π–D–π–A type molecules based on diphenylamine and carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property

Cited by 18 publications

References 50 publications

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Refined RGB Strategy for the Synthesis of Polymer‐Based Full Organic Luminescent Nanotubes with Broad Emission Bands

Contact Info

Product

Resources

About

Novel A–π–D–π–A type molecules based on diphenylamine and carbazole with large two-photon absorption cross section and excellent aggregation-induced enhanced emission property

Cited by 18 publications

References 50 publications

Novel Ferrocene‐Appended β‐Ketoimines and Related BF2 Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

Novel Ferrocene‐Appended β‐Ketoimines and Related BF2 Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

Enantioselective recognition of carboxylic acids by novel fluorescent triazine‐based thiazoles

Refined RGB Strategy for the Synthesis of Polymer‐Based Full Organic Luminescent Nanotubes with Broad Emission Bands

Contact Info

Product

Resources

About

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties

Novel Ferrocene‐Appended β‐Ketoimines and Related BF₂ Derivatives with Significant Aggregation‐Induced Emission and Second‐Order Nonlinear Optical Properties