A strategy to construct fluorescent non-aromatic small-molecules: hydrogen bonds contributing to the unexpected fluorescence

Guan, Ruifang; Dong, Baoli; Xu, Cui; Zhang, Hao; Cao, Duxia; Lin, Weiying

doi:10.1039/c9cc09906a

Cited by 17 publications

(12 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the last decade, unexpected visible fluorescence was discovered in various organic materials that were traditionally believed to be non‐fluorescent (due to their flexible structure). [ 30 ] These materials include, for example, gamma‐II crystalline, [ 31 ] propanedioyl dihydrazide (PDH), [ 32 ] aromatic (diphenylalanine, triphenylalanine (FFF)) and aliphatic peptides dileucine, [ 33 ] amyloid fibrils, [ 34,35 ] PEGylated hexaphenylalanine nanostructure (polyethylene glycol‐PEG), [ 36 ] elastin‐related polypeptide fibrils, [ 37 ] and other oligopeptides. [ 38 ] The source of this visible fluorescence is believed to be electron delocalization through hydrogen bonding in β‐sheet structure, [ 36 ] proton transfer, [ 39,40 ] and π–π and n–π coupling inter/intramolecular interactions.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

Handelman

Lapsker

Jacob

et al. 2020

Adv Funct Materials

View full text Add to dashboard Cite

The increasing interest in implantable medical devices that incorporate photonic components has accelerated the search for new, biocompatible optical materials at micro‐ and nano‐scale. This work proposes use of the polar amino acid L‐histidine as a candidate for bio‐photonic devices. L‐histidine is self‐assembled into diverse solid‐state crystallized microstructures, one of which—the elongated hexagonal microplate—is shown to have passive waveguiding capability of polarized light. The interaction of polarized light with histidine microplates having different orientations and thicknesses is studied from Stokes parameters and Mueller matrix. The linear birefringence of histidine microplates is estimated by using the theory of generalized Jones matrix for biaxial crystals. Visible fluorescence in heated histidine microplates is discovered and its origin is discussed. The phenomenon of passive waveguiding capability of polarized light by such an elongated hexagonal microplate means that the microplate can be used as a part of an optical switch. The findings show that besides the known chemical and biological characteristics of the amino acid histidine, it also has optical properties that can be exploited in multifunctional biophotonic applications, such as waveguides, polarizers, interconnects, and light sources.

show abstract

Section: Resultsmentioning

confidence: 99%

“…These bands were chosen in order to prove that the NH and CO groups are responsible for the visible fluorescence, as suggested in previous works. [ 42,32 ]…”

Section: Resultsmentioning

confidence: 99%

Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

Handelman

Lapsker

Jacob

et al. 2020

Adv Funct Materials

View full text Add to dashboard Cite

show abstract

“…The specific solvent effect on the AIE behavior of QLP-8 was investigated since the formation of the complex between solvent molecules and fluorophores was another important way to affect their properties. 37 Solitary pair electrons on the carbonyl group act as a good Lewis acid binding site, and the water molecule is a weak Lewis acid, so we wonder whether QLP-8 can form a complex with water to change its electronic transition mode. 23,38,39 Firstly, the electrostatic potential (ESP) of QLP-8 was calculated, and the result showed that the electron density was concentrated near the oxygen of the carbonyl group (Fig.…”

Section: The Effects Of Hydrogen Bonds On Their Aie Behaviormentioning

confidence: 99%

Intermolecular hydrogen bonds induce restriction of access to the dark state for triggering aggregation-induced emission

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Generally, these traditional AIEgens are often devised with the single or multiple aromatic motifs considering the strong electron conjugation, [63,64] yet there are also some peculiar AIEgens without aromatic systems. [65,66] Zhao et al unfolded the typical AIE effect form the extraordinarily nonaromatic annulene derivative cyclooctatetrathiophene (COTh). [67] The akin propeller-like conformations in TPE or HPS were not retained in the COTh.…”

Section: Pure Organic Aie Materialsmentioning

confidence: 99%

Aggregation‐induced emission materials for nonlinear optics

Han

et al. 2021

Aggregate

View full text Add to dashboard Cite

Aggregation‐induced emission (AIE) is a vital photophysical phenomenon that the luminogens in the concentrated or aggregated cases will engender the dramatically boosted emission in comparison with the dispersive states. Given this extraordinary emitting capacity exactly resolves the aggregation‐caused quenching (ACQ) situations residing in the traditional luminophores, the booming AIE luminogens have drawn tremendous interest owing to their advanced performances and colossal potential applications in various areas. Further exploitations of AIE molecules also drive the research interests in the midst of these AIE materials toward the nonlinear optical (NLO) regime. The combination of AIE and NLO effects have nurtured some unforeseen properties of AIE materials and extended their application spheres. Therefore, some NLO‐active AIE materials have been wielded in many crucial applications, for example, optical limiting, laser, bioimaging, and photodynamic therapy. Meanwhile, the impacts of aggregate on the NLO effect also deserve deep considerations and pursuits, and the modifications of aggregates promise an easy, efficient, and prompt avenue to tune the NLO properties of materials. The recent achievements and progress in the NLO properties of AIE materials have been summarized in this review. The second‐order and third‐order NLOs of the AIE materials have been introduced and their correlative applications have been discussed.

show abstract

A strategy to construct fluorescent non-aromatic small-molecules: hydrogen bonds contributing to the unexpected fluorescence

Abstract: Propanedioyl dihydrazide (PDH), traditionally believed to be non-fluorescent, was first discovered to emit substantial fluorescence in both the solid state and solvents.

Cited by 17 publications

References 23 publications

Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

Passive Polarized Light Guiding and Thermally Induced Visible Fluorescence in Histidine Microstructures with Optical Switching Function

Intermolecular hydrogen bonds induce restriction of access to the dark state for triggering aggregation-induced emission

Aggregation‐induced emission materials for nonlinear optics

Contact Info

Product

Resources

About