http://www.cnr.it/ontology/cnr/individuo/prodotto/ID173111

Synthesis multiphase, characterization and helicity control in chiral DACH-linked oligothiophenes (Articolo in rivista)

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Synthesis multiphase, characterization and helicity control in chiral DACH-linked oligothiophenes (Articolo in rivista) (literal)

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Alternative label

M. Melucci (1); G. Barbarella (1); M. Gazzano (1); M. Cavallini (2); F. Biscarini (2); A.Bongini (3); F. Piccinelli (3); M. Monari (3); M. Bandini (3); A. Umani-Ronchi (3); P. Biscarini (4) (2006)
Synthesis multiphase, characterization and helicity control in chiral DACH-linked oligothiophenes
in Chemistry (Weinh., Print); Wiley-VCH Verlag Gmbh, Weinheim (Germania)
(literal)

Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori

M. Melucci (1); G. Barbarella (1); M. Gazzano (1); M. Cavallini (2); F. Biscarini (2); A.Bongini (3); F. Piccinelli (3); M. Monari (3); M. Bandini (3); A. Umani-Ronchi (3); P. Biscarini (4) (literal)

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1. CNR, Ist Sintesi Organ & Fotoreatt, I-40129 Bologna, Italy 2. CNR, Ist Studio Mat Nanostrutt, Sez Bo, I-40129 Bologna, Italy 3. Univ Bologna, Dipartimento Chim G Ciamician, I-40126 Bologna, Italy 4. Univ Bologna, Dipartimento Chim Fis & Inorgan, I-40126 Bologna, Italy (literal)

Titolo

Synthesis multiphase, characterization and helicity control in chiral DACH-linked oligothiophenes (literal)

Abstract

A new class of chiral oligothiophenes is described. Mono-, bi-, ter-, and quarterthiophenes have been linked to enantiopure trans- 1,2-cyclohexanediamine (DACH) via diamino or diimino moieties. The stereochemistry of DACH, the type of linker, and oligothiophene size determine the conformational flexibility of these molecules and consequently their molecular and supramolecular helicity in solution and in the solid state. The case of diaminobis(bithiophene), which inverts helicity and shows chiral amplification in the transition from solution to film, is described in detail. Based on the combined use of circular dichroism in solution and in the solid state, single-crystal/thin-film X-ray diffraction, and polarized optical microscopy, a working mechanism has been proposed to explain this unexpected behavior. (literal)

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