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Issue 13, 2017
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Synthesis of steroidal molecular compasses: exploration of the controlled assembly of solid organic materials

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Abstract

In this work, five steroid-flanked derivatives of p-nitroaniline were studied to assess the influence of these rigid, chiral frameworks on the solid-state patterning of a dipolar dye, striving to drive the self-assembly of noncentrosymmetric crystals, which is of interest in the development of organic materials for nonlinear optics and piezoelectricity. The featured compounds were prepared using Sonogashira cross-coupling reaction with 17α-ethynyl steroids as a single key step. The structures of these new steroidal derivatives were established using one and two dimensional NMR 1H and 13C experiments. Single X-ray diffraction analysis unequivocally confirmed the presence of the steroidal molecular compasses 8 and 11, whose potential applicability for organic materials is preliminarily assessed via computational modeling, finding candidates for nonlinear optics, organic electronic materials and molecular recognition.

Graphical abstract: Synthesis of steroidal molecular compasses: exploration of the controlled assembly of solid organic materials

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Publication details

The article was received on 20 Jan 2017, accepted on 01 Mar 2017 and first published on 01 Mar 2017


Article type: Paper
DOI: 10.1039/C7CE00157F
Citation: CrystEngComm, 2017,19, 1771-1777
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    Synthesis of steroidal molecular compasses: exploration of the controlled assembly of solid organic materials

    N. Aguilar-Valdez, M. Maldonado-Domínguez, R. Arcos-Ramos, M. Romero-Ávila, R. Santillan and N. Farfán, CrystEngComm, 2017, 19, 1771
    DOI: 10.1039/C7CE00157F

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