Hydrogen-bonded dimer stacking induced emission of aminobenzoic acid compounds

Zhou, Tianlei; Li, Feng; Fan, Yuying; Song, Weifeng; Mu, Xiaoyue; Zhang, Hongyu; Wang, Yue

doi:10.1039/b900476a

Cited by 112 publications

(43 citation statements)

References 22 publications

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“…( O ) contains many more H ‐type than J ‐type aggregates; however, it is not clear at present why the ${\lambda {{{\rm fl}({\rm solid})\hfill \atop {\rm max}\hfill}}}$ (580 nm) of 2‐Crys. ( O ) is significantly redshifted compared with the ${\lambda {{{\rm fl}({\rm tol})\hfill \atop {\rm max}\hfill}}}$ (508 nm) of 2 46…”

Section: Resultsmentioning

confidence: 98%

A Series of π‐Extended Thiadiazoles Fused with Electron‐Donating Heteroaromatic Moieties: Synthesis, Properties, and Polymorphic Crystals

Kato

Furuya

Nitani

et al. 2014

Chemistry A European J

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π-Extended thiadiazoles 4-8 fused with various electron-donating heteroaromatic moieties have been designed and synthesized. Just like thiadiazoles 1-3 synthesized previously, 4-8 exhibit intramolecular charge-transfer (CT) interactions, moderate-to-good fluorescence quantum yields of up to 0.78, and electrochemical amphoterism. In comparison with 1-3, the benzannulation in thiadiazoles 4-7 moderately extends the π conjugation and significantly increases the stability of the cationic species formed upon electrochemical oxidation. The fluorescence quantum yields increase remarkably from 3 to 6 and 7 due to the efficient suppression of nonradiative intersystem crossing resulting from the benzannulation. The properties of 4-8 strongly reflect the different species annulated to the pyrrole rings, namely benzothiophene, naphthalene, and benzofuran. Eleven crystals, including poly- and pseudopolymorphic crystals of 1 (1-Crys.(Y) and 1-Crys.(G)), 2 (2-Crys.(O) and 2-Crys.(G)), 4 (4-Crys.(O) and 4-Crys.(G)), and 6 (6-Crys.(O) and 6-Crys.(G)), were obtained and characterized by X-ray crystallography. The fluorescence colors and efficiencies are distinct for each poly- and pseudopolymorph of 1, 2, 4, and 6. It has been suggested that both the extent of the electronic interactions in the π-stacked dimers and the presence of excitonic interactions originating in the 1D face-to-face slipped columns affect the fluorescence wavelengths of the poly- and pseudopolymorphs.

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Section: Resultsmentioning

confidence: 98%

A Series of π‐Extended Thiadiazoles Fused with Electron‐Donating Heteroaromatic Moieties: Synthesis, Properties, and Polymorphic Crystals

Kato

Furuya

Nitani

et al. 2014

Chemistry A European J

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“…Hydrogen bonding is an important non-covalent force often involved in the formation of supramolecular structures in the solid state. [57][58][59] In the area of photophysics research, it has been generally recognized that formation of hydrogen bonds between luminogens can rigidify their molecular structures and activate their RIR processes. This helps minimize the nonradiative energy losses of their excitons and maximize their probability of radiative transitions.…”

Section: Luminogens With Hydrogen Bondsmentioning

confidence: 99%

Aggregation-induced emission

2011

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Luminogenic materials with aggregation-induced emission (AIE) attributes have attracted much interest since the debut of the AIE concept in 2001. In this critical review, recent progress in the area of AIE research is summarized. Typical examples of AIE systems are discussed, from which their structure-property relationships are derived. Through mechanistic decipherment of the photophysical processes, structural design strategies for generating new AIE luminogens are developed. Technological, especially optoelectronic and biological, applications of the AIE systems are exemplified to illustrate how the novel AIE effect can be utilized for high-tech innovations (183 references).

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“…Peaks at 2960-2880 cm −1 belong to the aliphatic -C-H stretching vibration, peaks at about 1231 and 1100 cm −1 can be assigned to Ph-O-C and C-O-C stretching vibration, respectively, and the characteristic absorption of epoxy groups can be observed at about 908 and 843 cm −1 , indicating the successful functionalization of GO. Moreover, shifting of the peaks at 3441 −1 (-OH stretching vibration) to a lower wavenumber is direct evidence of H-bonding generation between the EHBPE and GO [27].…”

Section: Ftir Characterizationmentioning

confidence: 99%

One-Step Preparation of Hyperbranched Polyether Functionalized Graphene Oxide for Improved Corrosion Resistance of Epoxy Coatings

Miao

et al. 2019

Coatings

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In this paper, hyperbranched polyether functionalized graphene oxide (EHBPE-GO) was prepared by a facile one-step method. Fourier transform infrared spectroscopy (FTIR), X-ray diffractometry (XRD), thermogravimetric analyzer (TGA), and trans-mission electron microscopy (TEM) results confirmed the formation of EHBPE-GO. Then, EHBPE-GO was cured with phenolic amides at room temperature to prepare epoxy coatings. The corrosion resistance of epoxy coatings was investigated systematically by using electrochemical and traditional immersion methods. Results show that a small amount of EHBPE-GO (8 wt % of Diglycidyl ether of bisphenol A (DGEBA)) in epoxy coating achieves 50% higher improvement in acid-resistance than unmodified neat DGEBA resin. For the nanocomposite epoxy coating, the superior acid-resistance is attributed to the increased crosslink density and the impermeable 2D structure of EHBPE-GO. This work provides a facile strategy to develop the effective improved corrosion resistance nanofiller for epoxy coating.

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Hydrogen-bonded dimer stacking induced emission of aminobenzoic acid compounds

Abstract: A series of aminobenzoic acid crystals with stacking-induced emission properties has been achieved and the packing structures of the hydrogen-bonded acid dimers provided an explanation for the emission characteristics of the crystals.

Cited by 112 publications

References 22 publications

A Series of π‐Extended Thiadiazoles Fused with Electron‐Donating Heteroaromatic Moieties: Synthesis, Properties, and Polymorphic Crystals

A Series of π‐Extended Thiadiazoles Fused with Electron‐Donating Heteroaromatic Moieties: Synthesis, Properties, and Polymorphic Crystals

Aggregation-induced emission

One-Step Preparation of Hyperbranched Polyether Functionalized Graphene Oxide for Improved Corrosion Resistance of Epoxy Coatings

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