Details

Autor(en) / Beteiligte

• Aguilar-Valdez, Nancy
• Maldonado-Domínguez, Mauricio
• Arcos-Ramos, Rafael
• Romero-Ávila, Margarita
• Santillan, Rosa
• Farfán, Norberto

Titel

Synthesis of steroidal molecular compasses: exploration of the controlled assembly of solid organic materialsElectronic supplementary information (ESI) available: Synthetic procedures, 1H and 13C spectral data, theoretical band structure and density of states of 8, and modeling recognition of small molecules for 11. Crystallographic data for the structures in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 1525777 (8) and 152577

Erscheinungsjahr

2017-03

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 1 H and 13 C 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. Crystalline steroidal molecular compasses can be useful to develop self-assembled materials for molecular recognition and as organic semiconducting solids with extensive π-stacking.