α-Cyanostilbene: a multifunctional spectral engineering motif

Paramasivam, Mahalingavelar; Kanvah, Sriram

doi:10.1039/d2cp02686d

Cited by 40 publications

(23 citation statements)

References 149 publications

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“…HOMO iso‐surfaces are more distributed on the dithienopyrrol central donor unit, and LUMO iso‐surfaces are concentrated on the rhodanine terminal acceptor unit and spacers. The difference in the DFT calculated LUMO levels of the molecules are attributed to the intramolecular charge transfer transitions influenced by the π‐conjugated spacers [49] . For instance, ortho‐hydrogen‐induced dihedral deviation significantly affects the overlap of pi‐orbital interactions of the phenyl spacer unit, and it fails to stabilize the LUMO level over the thiophene counterparts.…”

Section: Resultsmentioning

confidence: 99%

“…The difference in the DFT calculated LUMO levels of the molecules are attributed to the intramolecular charge transfer transitions influenced by the π-conjugated spacers. [49] For instance, ortho-hydrogeninduced dihedral deviation significantly affects the overlap of pi-orbital interactions of the phenyl spacer unit, and it fails to stabilize the LUMO level over the thiophene counterparts. The optimized structures of TRh and PhRh with dihedral angles are represented in (Figure 6).…”

Section: Molecular Simulationsmentioning

confidence: 99%

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Facile synthesis of A‐π‐D‐π‐A architecture organic small molecules. Experimental and theoretical investigation of the effect of a π‐conjugated spacer

et al. 2023

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Understanding the structure‐property relationship is one of the critical factors in the practical design of organic small molecules for bulk heterojunction organic solar cells (BHJ‐OSCs). In this study, we designed and synthesized two low‐band‐gap organic small molecule donors, TRh and PhRh. To study the effect of the π‐conjugated spacer, the A‐π‐D‐π‐A architecture was constructed with an efficient dithienopyrrole donor (D) and rhodanine acceptor (A) units. Two types of π‐conjugated spacers, thiophene in TRh and phenyl in PhRh, are used to fine‐tune the various properties. A detailed investigation of the effect of π‐conjugated spacers on optoelectronic, thermal, and photovoltaic properties have carried out. TRh is planar, more conjugated, has a more prolonged absorption wavelength and leads to a low band gap of 1.48 eV. DFT studies demonstrate that TRh has lower BLA (Bond length alternation) and has more quinoid structure than PhRh. PhRh is thermally more stable than TRh. PhRh displayed a high glass transition temperature (Tg) at 193 °C and a 5% decomposition temperature at 402 °C. The inverted device architecture of BHJ‐OSCs blended with PC71BM displayed the PCE of 2.78% for TRh and 1.10% for PhRh. TRh : PC71BM blend exhibits higher hole and electron mobilities than PhRh : PC71BM blend.

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Section: Resultsmentioning

confidence: 99%

Section: Molecular Simulationsmentioning

confidence: 99%

Facile synthesis of A‐π‐D‐π‐A architecture organic small molecules. Experimental and theoretical investigation of the effect of a π‐conjugated spacer

et al. 2023

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“…(AIE) 9,10 . The aggregation-induced emission (AIE) behavior in cyanostilbenes is a direct result of their unique molecular structure, which is characterized by a rigid, planar conjugated backbone containing a cyano (-CN) group attached to the phenyl ring.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…This molecule 9, without any standard auxiliary groups such as alkyl chains, cholesterols, or amide units, formed stable organogels. The molecule also formed a two-component gel upon adding a second cyanostilbene molecule (10).…”

Section: Stimuli-responsive Sensing Ph Sensingmentioning

confidence: 99%

Functional α-Cyanostilbenes: Sensing to Imaging

Dahiwadkar

Kaloo

Kanvah³

2023

Synlett

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In recent years, there has been considerable interest in cyanostilbenes due to their unique photophysical properties. The compounds emit light when aggregating, commonly called aggregation-induced emission (AIE). This remarkable feature makes cyanostilbenes ideal for various sensing applications, especially in aqueous environments. The detection of various analytes, such as metal ions and nitroaromatic compounds, has been accomplished using these compounds through various sensing mechanisms from chelation-enhanced fluorescence to fluorescence quenching. Furthermore, cyanostilbenes have shown great promise in biological imaging applications and have been employed for intracellular imaging, tracking, and targeting of sub-cellular organelles. The development and utilization of cyanostilbenes can significantly impact advancing sensing and imaging technologies in both analytical and biological fields. This potential stems from the unique properties of cyanostilbenes, such as their AIE characteristic, which sets them apart from other compounds and makes them highly useful for various applications. Further exploration and development of cyanostilbenes could lead to the creation of novel sensing and imaging technologies with wide-ranging applications in both academic and industrial settings

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“…Aggregation-induced emission (AIE) based dyes have become a new powerful tool in biosensing and bioimaging due to their unique advantages such as strong emission in the aggregate state, high resistance to photobleaching, and long retention time in live samples. − Substantial efforts have been devoted to synthesizing distinct structure-functionalized AIE luminogens (AIEgens). − Among these, acrylonitriles are a family of D–A-based AIEgens and have been extensively investigated and applied in diverse applications (Scheme ). − For example, Zhao et al fabricated fluorescent nanoaggregates by the self-assembly of folic acid (FA) conjugated D–A acrylonitrile (1d-FA) for targeted three-photon bioimaging . A D–A–A-structured AIE-active acrylonitrile named Z-PPMNAN was reported by Tang’s group for reversible Z / E isomerization, photocyclization, and photodimerization under different stimuli .…”

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confidence: 99%

Donor–Acceptor–Acceptor-Conjugated Dual-State Emissive Acrylonitriles: Investigating the Effect of Acceptor Unit Order and Biological Imaging

et al. 2022

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The effect of acceptor unit order on the photophysical properties of two distinct donor–acceptor–acceptor conjugated fluorescent acrylonitriles, TPA-AN-PhBT and TPA-BT-ANPh, was systematically investigated. Compared with faintly emissive TPA-AN-PhBT in solution, TPA-BT-ANPh showed strong red-shifted fluorescence. TPA-AN-PhBT and TPA-BT-ANPh exhibited enhanced green and deep red emissions with remarkable fluorescence quantum yields up to 44% in the solid state. In addition, TPA-BT-ANPh possessed stronger two-photon absorption than TPA-AN-PhBT. Furthermore, these biocompatible dyes served as excellent fluorescent markers for specific lipid droplet imaging.

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α-Cyanostilbene: a multifunctional spectral engineering motif

Abstract: The remarkable photophysical phenomenon of aggregation-induced emission offers excellent strategies to obtain the molecular materials possessing unique spectral signatures such as high fluorescence intensity, excellent quantum yield, large Stokes shift...

Cited by 40 publications

References 149 publications

Facile synthesis of A‐π‐D‐π‐A architecture organic small molecules. Experimental and theoretical investigation of the effect of a π‐conjugated spacer

Facile synthesis of A‐π‐D‐π‐A architecture organic small molecules. Experimental and theoretical investigation of the effect of a π‐conjugated spacer

Functional α-Cyanostilbenes: Sensing to Imaging

Donor–Acceptor–Acceptor-Conjugated Dual-State Emissive Acrylonitriles: Investigating the Effect of Acceptor Unit Order and Biological Imaging

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