2‐aminothiophenes by the gewald reaction

Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D.

doi:10.1002/jhet.5570360203

Cited by 289 publications

(174 citation statements)

References 101 publications

Supporting

Mentioning

170

Contrasting

Unclassified

Order By: Relevance

“…2TPD has been prepared via a sixstep synthesis route, starting from a Gewald-type condensation between methyl pyruvate, ethyl 2-cyanoacetate, and sulfur to obtain the heterocyclic core structure, [40,41] as described in the Experimental Section and Figure S2 (Supporting Information). The polymers were end-capped and purified to remove any Pd or Sn residues, [42][43][44] as described in detail in the Supporting Information.…”

Section: Doi: 101002/adma201706584mentioning

confidence: 99%

Efficient Near‐Infrared Electroluminescence at 840 nm with “Metal‐Free” Small‐Molecule:Polymer Blends

et al. 2018

View full text Add to dashboard Cite

The development of efficient and biocompatible organic near-infrared emitters is attractive for many applications, spanning from photodynamic therapy [1] to light fidelity (Li-Fi) all-optical networking systems. [2][3][4] In particular, the range 700-1000 nm is interesting for medical applications, given the semitransparency of biological tissue in this spectral interval, [5] and we will specifically refer to this range as near-infrared (NIR) in the following text. Compared to conventional inorganic materials, organic NIR emitters are interesting also for their mechanical conformability, which makes them appealing for the integration in flexible and stretchable devices. [6] Furthermore, the metal-free organic light-emitting materials can be a cheap and biocompatible alternative to inorganic ones for application in wearable, implantable, or in vivo medical applications, such as for sensing of body temperature, heart and respiration rates, blood pressure, glucose level, and oxygenation. [7] In the search for ever-higher efficiencies, several classes of materials have been investigated, such as perovskite-structured methylammonium lead halides, [8][9][10] quantum dots, [11] and organometallic phosphorescent complexes. [12][13][14][15][16][17][18][19] However, although such hybrid materials afford substantial electroluminescence (EL) external quantum efficiency (EQE) in the NIR, in some cases exceeding 10% [8,10] or even 20% or so, [13] their use of heavy, toxic, and/or costly metals is not ideal for manufacturing, sustainability, environmental impact, and, in perspective, biocompatibility. Furthermore, in such hybrid systems, and in general in materials that leverage triplet excitons to boost the EQE, [20,21] exciton recombination dynamics typically fall in the hundreds of nanoseconds or even in the microsecond (or longer) range, which intrinsically limits the bandwidth when integrated in devices for telecommunications. For Li-Fi applications, [2][3][4] fluorescent molecular and polymeric materials are preferred, given that the typical fluorescence lifetime of these materials is of the order of few nanoseconds or less, thereby ideally allowing data transmission rates up to the Gb s −1 regime.In the last decade, scientists have attempted different strategies to develop heavy-metal-free NIR fluorescent organic light-emitting diodes (OLEDs), with chemical design essentially revolving around the careful combination of donor and acceptor groups to both tune the spectral range (up to 1000 nm) and maximize the EQE. [22][23][24][25][26][27][28][29][30][31][32][33] Very recently, we have, for Due to the so-called energy-gap law and aggregation quenching, the efficiency of organic light-emitting diodes (OLEDs) emitting above 800 nm is significantly lower than that of visible ones. Successful exploitation of triplet emission in phosphorescent materials containing heavy metals has been reported, with OLEDs achieving remarkable external quantum efficiencies (EQEs) up to 3.8% (peak wavelength > 800 nm). For OLEDs incorporating f...

show abstract

Section: Doi: 101002/adma201706584mentioning

confidence: 99%

Efficient Near‐Infrared Electroluminescence at 840 nm with “Metal‐Free” Small‐Molecule:Polymer Blends

et al. 2018

View full text Add to dashboard Cite

show abstract

“…2-Aminothiophene derivatives are important intermediates in the synthesis of avariety of agrochemicals, dyes and pharmacologically active compounds [1]. The most convergent and well established classical approach for the preparation of 2-aminothiophenes is Gewald's method [2,3], which involves the multicomponent condensation of aketone with an activated nitrile and elemental sulfur in the presence of diethylamine as acatalyst.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of diethyl 2-amino-4-methylthiophene-3,5- dicarboxylate, C11H15NO4S

Zhang¹,

Jiao²

2010

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

“…The Gewald method, involves the reaction of ketones, aldehydes or 1,3-dicarbonyl species with activated nitriles and elemental sulfur in the presence of an amine base. This method is an improvement over other existing routes for the synthesis of 2-aminothiophenes [10,11].…”

Section: Introductionmentioning

confidence: 97%

A Solvent-Free, One-Step, One-Pot Gewald Reaction for Alkyl-aryl Ketones via Mechanochemistry

2014

View full text Add to dashboard Cite

show abstract

2‐aminothiophenes by the gewald reaction

Abstract: The review presents the most elegant and promising set of synthetic routes for the synthesis of 2‐aminothiophenes by the Gewald reaction. Applications of this facile methodology to pharmaceuticals and dyestuffs have been demonstrated.

Cited by 289 publications

References 101 publications

Efficient Near‐Infrared Electroluminescence at 840 nm with “Metal‐Free” Small‐Molecule:Polymer Blends

Efficient Near‐Infrared Electroluminescence at 840 nm with “Metal‐Free” Small‐Molecule:Polymer Blends

Crystal structure of diethyl 2-amino-4-methylthiophene-3,5- dicarboxylate, C11H15NO4S

A Solvent-Free, One-Step, One-Pot Gewald Reaction for Alkyl-aryl Ketones via Mechanochemistry

Contact Info

Product

Resources

About