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Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment
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Abstract
The synthesis and analysis of the title dye is described so as to make it easy for instructors to select exercises that best fit their curricular needs (organic synthesis, instrumental analysis, and comparative analysis of other materials). The relatively simple (Henry reaction) synthesis produces attractive, flaky, glistening, brick-red crystals that can be studied a number of ways including absorbance, fluorescence, and NMR spectroscopies. Direct observation of the interesting and unique effects of solvatochromism will benefit students' understanding of the causes of solvatochromism and of the general theories governing the electronic processes involved in absorption and fluorescence. The dye is also useful for studying the polarity of macromolecular media like detergents, surfactants, micelles, and cyclodextrins in aqueous solution. This can be a particularly interesting way of comparing types of organized media such as consumer soaps and detergents and is best suited for the advanced undergraduate.
Keywords (Audience):
Second-Year UndergraduateKeywords (Domain):
Laboratory InstructionKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
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This article has been cited by 6 ACS Journal articles (5 most recent appear below).
In situ Formation of Thermally Stable, Room-Temperature Ionic Liquids from CS2 and Amidine/Amine Mixtures.
Tao Yu, Taisuke Yamada, and Richard G. WeissChemistry of Materials2010 22 (19), 5492-5499In situ Formation of Thermally Stable, Room-Temperature Ionic Liquids from CS2 and Amidine/Amine Mixtures.
Tao Yu, Taisuke Yamada, and Richard G. WeissChemistry of Materials2010 22 (19), 5492-5499Amidinium dithiocarbamates salts with diverse structures are prepared in situ by adding one equivalent of CS2 to an equimolar mixture of two nonionic molecules, an amidine and an amine. Many of the salts made in this way are room temperature ionic liquids ...
Carbon Dioxide and Molecular Nitrogen as Switches between Ionic and Uncharged Room-Temperature Liquids Comprised of Amidines and Chiral Amino Alcohols
Tao Yu, Taisuke Yamada, Gabriel C. Gaviola and Richard G. WeissChemistry of Materials2008 20 (16), 5337-5344Carbon Dioxide and Molecular Nitrogen as Switches between Ionic and Uncharged Room-Temperature Liquids Comprised of Amidines and Chiral Amino Alcohols
Tao Yu, Taisuke Yamada, Gabriel C. Gaviola and Richard G. WeissChemistry of Materials2008 20 (16), 5337-5344Mixtures of amidines and amino alcohols react efficiently with carbon dioxide, producing ionic liquids which do not solidify to −20 °C. They return to amidine/amino alcohol mixtures when warmed to ca. 50 °C in the air or bubbled with nitrogen gas.
Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions
James V. McCullagh and Kelly A. DaggettJournal of Chemical Education2007 84 (11), 1799Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions
James V. McCullagh and Kelly A. DaggettJournal of Chemical Education2007 84 (11), 1799The synthesis of dyes has long been a popular topic in organic chemistry laboratory experiments because it allows students to see first hand that reactions learned in class can be used to make compounds with useful applications. In this experiment ...
Reversible, Room-Temperature, Chiral Ionic Liquids. Amidinium Carbamates Derived from Amidines and Amino-Acid Esters with Carbon Dioxide
Taisuke Yamada, Paul Joseph Lukac, Tao Yu, and Richard G. WeissChemistry of Materials2007 19 (19), 4761-4768Reversible, Room-Temperature, Chiral Ionic Liquids. Amidinium Carbamates Derived from Amidines and Amino-Acid Esters with Carbon Dioxide
Taisuke Yamada, Paul Joseph Lukac, Tao Yu, and Richard G. WeissChemistry of Materials2007 19 (19), 4761-4768The properties of a new class of chiral, room-temperature, ionic liquids (RTILs) are described. They are made from easily synthesized, readily available materials and can be transformed reversibly to their nonionic liquid states. The nonionic liquids ...
Reversible, Room-Temperature Ionic Liquids. Amidinium Carbamates Derived from Amidines and Aliphatic Primary Amines with Carbon Dioxide
Taisuke Yamada, Paul Joseph Lukac, Mathew George, and Richard G. WeissChemistry of Materials2007 19 (5), 967-969Reversible, Room-Temperature Ionic Liquids. Amidinium Carbamates Derived from Amidines and Aliphatic Primary Amines with Carbon Dioxide
Taisuke Yamada, Paul Joseph Lukac, Mathew George, and Richard G. WeissChemistry of Materials2007 19 (5), 967-969
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- Received: August 03, 2009
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