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Melucci M, Barbarella G, Gazzano M, et al. Synthesis, multiphase characterization, and helicity control in chiral DACH-linked oligothiophenes. Chemistry. 2006;12(28):7305-12doi: 10.1002/chem.200600312.
Melucci, M., Barbarella, G., Gazzano, M., Cavallini, M., Biscarini, F., Bongini, A., Piccinelli, F., Monari, M., Bandini, M., Umani-Ronchi, A., & Biscarini, P. (2006). Synthesis, multiphase characterization, and helicity control in chiral DACH-linked oligothiophenes. Chemistry (Weinheim an der Bergstrasse, Germany), 12(28), 7305-12. https://doi.org/10.1002/chem.200600312
Melucci, Manuela, et al. "Synthesis, multiphase characterization, and helicity control in chiral DACH-linked oligothiophenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 12,28 (2006): 7305-12. doi: https://doi.org/10.1002/chem.200600312
Melucci M, Barbarella G, Gazzano M, Cavallini M, Biscarini F, Bongini A, Piccinelli F, Monari M, Bandini M, Umani-Ronchi A, Biscarini P. Synthesis, multiphase characterization, and helicity control in chiral DACH-linked oligothiophenes. Chemistry. 2006 Sep 25;12(28):7305-12. doi: 10.1002/chem.200600312. PMID: 16944542.
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Chemistry. 2006 Sep 25;12(28):7305-12. doi: 10.1002/chem.200600312.

Synthesis, multiphase characterization, and helicity control in chiral DACH-linked oligothiophenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Manuela Melucci, Giovanna Barbarella, Massimo Gazzano, Massimiliano Cavallini, Fabio Biscarini, Alessandro Bongini, Fabio Piccinelli, Magda Monari, Marco Bandini, Achille Umani-Ronchi, Paolo Biscarini

Affiliations

  1. Istituto per la Sintesi Organica e la Fotoreattività (ISOF), Consiglio Nazionale Ricerche, Via Gobetti 101, 40129 Bologna, Italy. [email protected]

PMID: 16944542 DOI: 10.1002/chem.200600312

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.

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