4 years ago

Photocontrol over Molecular Shape: Synthesis and Photochemical Evaluation of Glycoazobenzene Macrocycles

Photocontrol over Molecular Shape: Synthesis and Photochemical Evaluation of Glycoazobenzene Macrocycles
Julia Hain, Guillaume Despras, Sven Ole Jaeschke
Reversible shape switching due to external stimuli is an attractive property for the control of molecular features. Hence, we aimed at macrocycles to investigate photoswitching of molecular shape. We prepared the first carbohydrate-based macrocycles comprising a photoresponsive azobenzene hinge. These macrocycles were readily obtained by cyclization of isothiocyanate-armed bis-azobenzene glycosides with piperazine. The unprotected macrocycles exhibit favorable photochromic properties in water and DMSO. Notably, the efficient transcis isomerization results in a remarkable shape transformation of the molecule. Additionally, the structure is characterized by restricted conformational freedom of the backbone, resulting in a single main conformer in each geometrical state (trans or cis). Measurement of optical rotation values and circular dichroism spectra revealed a tremendous change in chirality upon photoisomerization, with a strong helical induction in the cis state. These findings highlight the applicability of the new macrocycles as chiroptical molecular switches. Light switch: The first photoswitchable glycomacrocycles were described and they undergo remarkable molecular shape and chirality changes upon photoisomerization of an azobenzene hinge (see figure).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701232

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