Selective “turn-on” probes for CN − based on a fluorophore skeleton of 1,3-dihydroisobenzofuran

Shang, Xue Song; Li, Nian Tai; Guo, Zhi Qian; Liu, Pei Nian

doi:10.1016/j.dyepig.2016.04.051

Cited by 16 publications

(4 citation statements)

References 69 publications

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“…Dihydroisobenzofuran structure acts as a core skeleton in many natural products, bioactive compounds or functional molecules, for example, xylarinol B, escitalopram, matriisobenzofuran, thunberginol F 7- O -β- d -glucopyranoside, and functional material. , Nowadays, the efficient synthetic routes to dihydroisobenzofuran derivatives are usually by performing at high temperatures , or using metal-catalyzed approaches, while non-metal-mediated methods under mild reaction conditions are rarely reported . Yamada et al reported an elegant silver-catalyzed C–C bond formation with carbon dioxide to afford dihydroisobenzofuran derivatives (Scheme , a) .…”

Section: Introductionmentioning

confidence: 99%

TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

et al. 2019

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A novel methodology for the stereoselective synthesis of dihydroisobenzofuran derivatives is described in this paper. The procedure was realized by the bifunctional TBAF catalyzed selective O-nucleophilic cyclization of enaminone with intramolecular alkyne under mild and non-metal-mediated conditions. The results of control experiments suggested that the cation−π interaction and basicity, offered by TBAF, might be indispensable for the isomerization of enaminone and the formation of carbon–oxygen bond.

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Section: Introductionmentioning

confidence: 99%

TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

et al. 2019

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“…Small organic molecules have great advantages as luminescent materials because their emissive characteristics can be easily optimized synthetically. In particular, hetero- ISSN 2053ISSN -2296 # 2018 International Union of Crystallography cyclic compounds with a carbonitrile group have attracted much attention as emissive fluorophores (Shang et al, 2016;Maurya & Singh, 2017).…”

Section: Introductionmentioning

confidence: 99%

Structural and optical profile of a multifunctionalized 2-pyridone derivative in a crystal engineering perspective

Joy

Anabha²,

Gopi

et al. 2018

Acta Crystallogr C

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The supramolecular structural features of organic molecules are very important with regard to their widespread properties in both solids and solutions. Herein, we describe the synthesis of a novel multifunctional 2-pyridone derivative, namely 6-(4-chlorophenyl)-5-formyl-4-methylsulfanyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, CHClNOS, denoted P1, and its structural features were established through X-ray crystallography. A Hirshfeld surface analysis followed by a two-dimensional fingerprint plot analysis was carried out. A frontier molecular orbital investigation and natural bond orbital (NBO) calculations explored the charge-transfer interactions associated with the molecular system. The optical properties of the 2-pyridone derivative were elucidated through UV-Vis absorption and emission spectroscopy, indicating a strong blue emissive nature with a colour purity of 82.5%, a short-lived lifetime and a large Stokes shift. Time-dependent density functional theory (TD-DFT) was used to gain some insight into the absorption behaviour and emissive characteristics of P1.

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“…Understanding the photophysical properties of the 1,3‐dihydroisobenzofuran moiety is important owing to the fact that this scaffold is prevalent in antidepressant drug Citalopram . Recently, Shang et al., investigated the photophysical properties of 1,3‐bisarylidene‐1,3‐dihydroisobenzofuran derivatives and judiciously utilized the observed fluorescence for detection of cyanide ion . At this juncture, we envisaged that in order to understand the fundamental photophysical contribution of the 1,3‐dihydroisobenzofuran scaffold to the overall photophysics of such molecular dyes it is better to consider only the part structure of the 1,3‐bisarylidene‐1,3‐dihydroisobenzofuran derivatives.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent 1-Arylidene-1,3-dihydroisobenzofuran: Ligand-Free Palladium Nanoparticles, Catalyzed Domino Synthesis and Photophysical Studies

et al. 2017

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The present work describes synthesis and photophysical studies of a class of fluorophores containing biologically relevant 1,3-dihydroisobenzofuran scaffold. Ligand-free palladium nanoparticles have been utilized for domino synthesis of 1arylidene-1,3-dihydroisobenzofurans from 2-iodobenzyl alcohol and terminal arylacetylenes under mild reaction conditions. Reaction of terminal alkylacetylenes with 2-iodobenzyl alcohol however, provided only the Sonogashira products (2-(alk-1ynyl)phenyl)methanols. The 1-arylidene-1,3-dihydroisobenzofur-an derivatives showed structured fluorescence spectra in nonpolar cyclohexane, originated from a locally excited state and structureless emission in polar acetonitrile involving intramolecular charge transfer process. The vibronic structures in the locally excited emission were confined to the ring C=C stretching of the dyes. A detailed structure-property relationship of the 1-arylidene-1,3-dihydroisobenzofuran dyes is presented in this study.[a] Dr.

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Selective “turn-on” probes for CN − based on a fluorophore skeleton of 1,3-dihydroisobenzofuran

Cited by 16 publications

References 69 publications

TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

TBAF-Catalyzed O-Nucleophilic Cyclization of Enaminones: A Process for the Synthesis of Dihydroisobenzofuran Derivatives

Structural and optical profile of a multifunctionalized 2-pyridone derivative in a crystal engineering perspective

Fluorescent 1-Arylidene-1,3-dihydroisobenzofuran: Ligand-Free Palladium Nanoparticles, Catalyzed Domino Synthesis and Photophysical Studies

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