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New Trends in Chemistry and Application of Aromatic and Related Selenaheterocycles

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Part of the book series: Topics in Heterocyclic Chemistry

Abstract

Progress in the chemistry of compounds having π-conjugated selenaheterocyclic systems is presented. The review concentrates on the most representative selenaheterocycles: selenophene, selenazoles, selenadiazoles, as well as on seleninium salts. Their aromaticity is discussed and the chemical properties are illustrated by the most characteristic reactions. Various approaches to the synthesis of different selenaaromatic ring systems are presented. A number of selenaaromatic compounds and their nonconjugated analogs are indicated as reagents and catalysts for organic synthesis, as biological response modifiers of practical importance as pharmaceuticals, and as new materials for electronics.

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Abbreviations

AIBN:

α,α′-Azaisobutyronitrile

ASE:

Aromatic stabilization energy;

BETS:

Bis(ethylenedithio)tetraselenafulvalene;

COD:

Cyclooctadiene;

DMAD:

Dimethyl acetylenedicarboxylate;

DRE:

Dewar resonance energy;

GPx:

Glutathione peroxidase;

HMDS:

Hexamethyldisilazane;

HMPA:

Hexamethylphosphoric triamide;

HOMA:

Harmonic oscillator model of aromaticity;

IL:

Interleukine;

IFN:

Interferon;

LDA:

Lithium diisopropylamide;

LHMDS:

Lithium hexamethyldisilazide;

MCPBA:

m-Chloroperoxybenzoic acid;

MIC:

Minimal inhibitory concentration;

NICS:

Nucleus independent chemical shifts;

OLED:

Organic light-emitting diode;

OTFT:

Organic thin film transistor;

PBL:

Peripheral blood leukocytes;

PDSE:

Poly-1,2-bis(seleninyl)ethene;

PEDOS:

Poly-3,4-ethylenedioxyselenophene;

PEDOT:

Poly-3,4-ethylenedioxythiophene;

PS:

Polyselenophene;

RF-ID:

Radio frequency identification;

TBHP:

t-Butyl hydroperoxide;

TMEDA:

1,1,4,4-Tetramethylethylenediamine;

TMSF:

Tetramethylselenafu-lvalene;

TNF:

Tumor necrosis factor

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  1. J. Młochowski Department of Organic Chemistry, Faculty of Chemistry, Wrocław University of Technology, ul. Wybrzeże Wyspiańskiego50-370, Wrocław, Poland

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Młochowski, J., Giurg, M. (2008). New Trends in Chemistry and Application of Aromatic and Related Selenaheterocycles. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_7

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