Harnessing sun for catalyst and sensitizer free regio- and stereo-selective [2+2] cycloaddition

Jha, Kunal Kumar; Dutta, Sanjay; Sar, Saibal; Sen, Subhabrata; Munshi, Parthapratim

doi:10.1016/j.tet.2018.10.065

Cited by 5 publications

(5 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A mixture of 4-(dimethylamino) benzaldehyde (0.50 g, 3.35 mmol) and 4-nitrohenylacetonitrile (0.54 g, 3.35 mmol) was refluxed using piperidine as a basic catalyst in ethanol at 70 °C for 3 h as reported earlier. − The filtrate was evaporated under reduced pressure to yield a dark red crude product which was purified by column chromatography packed with silica. The desired product was obtained as a red crystalline solid (Scheme SI).…”

Section: Methodsmentioning

confidence: 99%

Structure–Property Relationship in an Organic Semiconductor: Insights from Energy Frameworks, Charge Density Analysis, and Diode Devices

Jha

Yadav

Srivastava

et al. 2019

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

A lightweight organic material, trans-4′-dimethylamino-4-nitro-α-cyanostilbene, exhibits notable charge carrier mobility (∼10–4 cm2 V–1 s–1). The non-centrosymmetric material also displays moderate second harmonic generation activity. This is one of the rarest examples of small organic materials displaying semiconductor characteristics. The charge-transfer pathway as elucidated via high-resolution single-crystal X-ray diffraction data based “energy frameworks” and “experimental charge density” analyses is assessed by measuring the charge carrier mobility using the space charge limited current technique on pure single-crystal diode devices. These advanced structural analyses clearly demonstrate that charge transport in organic crystals is purely governed by its molecular packing, especially the π–π stacking geometry. The balanced ambipolar charge transport behavior makes this highly soluble and thermally stable organic crystal promising for applications in optoelectronic devices. Moreover, this report introduces the crucial role of energy frameworks and charge density analyses for fundamental understanding of the structure–property relationship in organic semiconductors.

show abstract

Section: Methodsmentioning

confidence: 99%

Structure–Property Relationship in an Organic Semiconductor: Insights from Energy Frameworks, Charge Density Analysis, and Diode Devices

Jha

Yadav

Srivastava

et al. 2019

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

show abstract

“…The title compound 1 was synthesized following the protocol of its other analogues. , The details of the synthesis and its characterization are given in the Supporting Information. A range of HPLC-grade solvents with varying polarity at room temperature (22–25 °C) and low temperature (3–6 °C) were considered for the crystallization of 1 using the slow evaporation method (Table ).…”

Section: Methodsmentioning

confidence: 99%

“…The π-conjugated stilbene scaffolds exhibit polymorphic and chromic behavior, 32−35 non-linear optical properties, 36 semiconducting behavior, 37 undergo photo dimerization, and display bioactivity. 38 Some experimental and computational studies on solvatochromic properties of D−π−A organic structures are also reported in the literature. 39,40 Here, we report the systematic investigations of eight solvates and the parent molecule of a π-conjugated cyanosubstituted nitro stilbene derivative, 1 (Scheme 1).…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solvatochromism and Reversible Solvent Exchange Phenomena in Solvatomorphic Organic Chromophore Crystals

Jha

Kumar

Munshi

2023

Crystal Growth & Design

Self Cite

View full text Add to dashboard Cite

Solvatomorphs or solvates are common in pharmaceutical compounds, and solvatochromism is often reported in solution. The present study reports eight solvates of (Z)-3-(3-hydroxy-4-methoxy phenyl)-2-(4-nitrophenyl) acrylonitrile, a π-conjugated push−pull organic chromophore. The solvates containing (i) chlorobenzene, (ii) ethyl-acetate, (iii) 1,4dioxane, (iv) acetone, (v) acetonitrile, (vi) N,N-dimethylformamide, (vii) N-methyl-2pyrrolidine, and (viii) dimethyl sulfoxide as solvents in their crystal lattices display the solvatochromism effect. All the solvates and the parent form are systematically characterized using spectroscopic, crystallization, thermal analysis, single-crystal X-ray diffraction techniques, and structural analysis. The solvatomorphs reported here are either non-isostructural or have a low degree of isostructurality, except for one pair for which a three-dimensional isostructurality is observed. The structural stabilities of the solvates are correlated with their molecular packing, crystal voids, and thermal properties. Moreover, the possible mechanism behind the solvatochromism and the reversible solvent exchange phenomena have been explored. This report is one of the rarest series of solvatomorphs exhibiting reversible solvent exchange properties and solvatochromic effect both in crystal and solution. Such studies are crucial for the dye and pharmaceutical industries dealing with various solvents and the formulation of drugs in solvated forms, respectively.

show abstract

“…The rigid cyclobutane backbone is an important structural scaffold for biologically active compounds and a popular synthetic target for drug development. − The photoinduced [2 + 2] cycloaddition reaction is the most atom-economical and straightforward approach for constructing this motif. , However, this method suffers from poor selectivity and therefore, a potentially tedious separation, especially for the synthesis of multi-cyclic isomers . CPs can supply stereo-directive templating through olefin pre-arrangement; − however, the preorganization of multiple CC pairs is challenging to manage at the molecular level because of the dynamic nature of CC bonds .…”

Section: Introductionmentioning

confidence: 99%

Coordination Polymer-Mediated Molecular Surgery for Precise Interconversion of Dicyclobutane Compounds

et al. 2022

View full text Add to dashboard Cite

A Cd(II)-based coordination polymer {[Cd2(5-F-1,3-bpeb)2(FBA)4]·H2O} n (CP 1 ) was obtained from Cd(II) salt, 5-fluoro-1,3-bis[2-(4-pyridyl)ethenyl]benzene (5-F-1,3-bpeb), and p-fluorobenzoic acid (HFBA). Within the one-dimensional chain structure of CP 1 , a pair of 5-F-1,3-bpeb was arranged in a face-to-face style. Upon UV irradiation and heat treatment, multiple cyclobutane isomers, including specific monocyclobutanes (1 with an endo-cyclobutane ring in CP 1 -1 and 1′ with an exo-cyclobutane ring in CP 1 -1′) and dicyclobutanes (endo,endo-dicyclobutane 2α in CP 1 -2α, exo,endo-dicyclobutane 2β in CP 1 -2β, and exo,exo-dicyclobutane 2γ in CP 1 -2γ) were stereoselectively produced. These isomers could be interconverted inside the CP via cutting/coupling specific bonds, which may be regarded as a type of molecular surgery. The precision of cutting/coupling relied on the thermal stability of the cyclobutanes and the alignment of the reactive alkene centers. The conversion processes were tracked through nuclear magnetic resonance, in situ powder X-ray diffraction, and IR spectroscopy. This approach can be considered as skeletal editing to construct complex organic compounds directly from one precursor.

show abstract

Harnessing sun for catalyst and sensitizer free regio- and stereo-selective [2+2] cycloaddition

Cited by 5 publications

References 42 publications

Structure–Property Relationship in an Organic Semiconductor: Insights from Energy Frameworks, Charge Density Analysis, and Diode Devices

Structure–Property Relationship in an Organic Semiconductor: Insights from Energy Frameworks, Charge Density Analysis, and Diode Devices

Solvatochromism and Reversible Solvent Exchange Phenomena in Solvatomorphic Organic Chromophore Crystals

Coordination Polymer-Mediated Molecular Surgery for Precise Interconversion of Dicyclobutane Compounds

Contact Info

Product

Resources

About