2020
DOI: 10.1021/acs.joc.0c00867
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Synthesis and Solid-State Dynamics of a Crystalline Steroid Molecular Rotor without the Alkyne Axle: Steroid Dimers Based on a 1,4-Di(1,3-dioxan-2-yl)benzene Moiety

Abstract: Two diastereomeric crystalline steroid dimers were obtained by acid-catalyzed double acetalization of (20S)-5αpregnan-3β,16β,20-triol 3-monoacetate with terephtalaldehyde. These compounds were characterized by NMR in solution, MS, single-crystal X-ray diffraction, and variable-temperature solid-state NMR by 13 C cross-polarization magic angle spinning (CPMAS). While the phenylene rotator in the SR diastereomer remains static even at 373 K, the RR isomer shows a slow rotational process of the phenylene ring at … Show more

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Cited by 11 publications
(17 citation statements)
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“…In agreement with X-ray diffraction experiments, the crosspolarization magic-angle spinning (CP-MAS) 13 C{ 1 H} spectrum of SMR-3 exhibits two sets of signals for the two crystallographically non-equivalent molecules in the asymmetry unit (Z′ = 2). Furthermore, the two steroid fragments in one molecule of SMR-3 are also crystallographically nonequivalent, which results in four 13 C{ 1 H} signals for every position in the steroid fragment (Figure 6a and Figure S25).…”
Section: The Journal Of Organic Chemistrysupporting
confidence: 74%
“…In agreement with X-ray diffraction experiments, the crosspolarization magic-angle spinning (CP-MAS) 13 C{ 1 H} spectrum of SMR-3 exhibits two sets of signals for the two crystallographically non-equivalent molecules in the asymmetry unit (Z′ = 2). Furthermore, the two steroid fragments in one molecule of SMR-3 are also crystallographically nonequivalent, which results in four 13 C{ 1 H} signals for every position in the steroid fragment (Figure 6a and Figure S25).…”
Section: The Journal Of Organic Chemistrysupporting
confidence: 74%
“…Pursuing this and other goals, we have recently described the synthesis and the study of the properties of modified BA derivatives as well as several steroid dimers . Herein, we describe a dimeric BA derivative in which the two steroid cores are bridged by the fluorescent 2,2′-[1,4-phenylenebis­(ethyne-2,1-diyl)]­dibenzoyl fragment attached to the hydroxyl groups at positions C-3α and C-3′α (Scheme ).…”
Section: Introductionmentioning
confidence: 99%
“…As predicting the crystal structure of complex molecules such as SMRs remains extremely challenging nowadays, further general crystal engineering criteria are needed to help avoiding their self‐assembly into ‘static’ crystals, that are incapable of displaying fast rotational dynamics. Along this line, interesting discrete structural modifications have been explored, including diverse strategies to obtain macrocyclic SMRs with further shielding of the rotation, [10c,g,h,17] as well as alternative ways to join the stator and the rotator other than by using ethynyl axles [10b,e] …”
Section: Introductionmentioning
confidence: 99%