From Capsule to Helix: Guest-Induced Superstructures of Chiral Macrocycle Crystals
Type
ArticleAuthors
Dey, Avishek
Chand, Santanu
Alimi, Lukman Olawale

Ghosh, Munmun
Cavallo, Luigi

Khashab, Niveen M.

KAUST Department
Advanced Membranes and Porous Materials Research CenterChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Smart Hybrid Materials (SHMs) lab
Date
2020-07-31Online Publication Date
2020-07-31Print Publication Date
2020-09-16Embargo End Date
2021-08-01Permanent link to this record
http://hdl.handle.net/10754/664547
Metadata
Show full item recordAbstract
The prediction, control, understanding and elucidation of phase transition from gel to crystal is in high demand for the de-velopment of various functional materials with macroscopic properties. Here, we show a detailed and systematic description of the self-assembly process of enantiopure trianglimine macrocyclic host from gel to single crystals. This proceeds via an unprecedented formation of capsule-like or right-handed helix superstructures as metastable products, depending on the nature of the guest molecule. Mesitylene promotes the formation of capsule-like superstructures; whereas, toluene results in the formation of helices as intermediates during the course of crystallization. Single crystal results demonstrate that the crystals obtained via the direct self-assembly from the gel phase are different from the crystals obtained from the stepwise assembly of the intermediate superstructures. Hence, investigating the phase-transition superstructures that self-assemble through the process of crystallization can unravel new molecular ordering with unexplored host-guest interactions. Such understanding will provide further tools to control hierarchical assemblies at the molecular level and consequently design or dictate the properties of evolved materials.Citation
Dey, A., Chand, S., Alimi, L. O., Ghosh, M., Cavallo, L., & Khashab, N. M. (2020). From Capsule to Helix: Guest-Induced Superstructures of Chiral Macrocycle Crystals. Journal of the American Chemical Society. doi:10.1021/jacs.0c05776Sponsors
This work was supported by King Abdullah University of Science and Technology (KAUST). We are thankful to Dr. Bholanath Maity, KAUST Catalysis Center (KCC) for fruitful discussions on theoretical calculations and studies.Publisher
American Chemical Society (ACS)Additional Links
https://pubs.acs.org/doi/10.1021/jacs.0c05776Relations
Is Supplemented By:- [Dataset]
Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098788: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYVJ. DOI: 10.5517/ccdc.csd.cc28fyvj Handle: 10754/686949 - [Dataset]
Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098789: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYWK. DOI: 10.5517/ccdc.csd.cc28fywk Handle: 10754/686950 - [Dataset]
Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098790: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYXL. DOI: 10.5517/ccdc.csd.cc28fyxl Handle: 10754/686951 - [Dataset]
Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098791: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYYM. DOI: 10.5517/ccdc.csd.cc28fyym Handle: 10754/686952 - [Dataset]
Dey, Avishek, Chand, Santanu, Alimi, Lukman O., Ghosh, Munmun, Cavallo, Luigi, & Khashab, Niveen M. (2021). CCDC 2098792: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC28FYZN. DOI: 10.5517/ccdc.csd.cc28fyzn Handle: 10754/686953
ae974a485f413a2113503eed53cd6c53
10.1021/jacs.0c05776