Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 25, Issue 26, Pages 6584-6590Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201900371
Keywords
crystal engineering; halogen bonds; luminescence; noncovalent interactions; supramolecular chemistry
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Funding
- Shanghai Natural Science Foundation [18ZR1447900]
- Youth Innovation Promotion Association CAS [2016257]
- CAS Key Technology Talent Program
- SANOFI-SIBS Scholarship
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Research on new supramolecular synthons facilitates the progress of materials design. Herein, the ability of sp(2) carbonyl oxygen atoms to act as halogen-bond acceptors was established through cocrystallization. Four sets of carbonyl compounds, including aldehydes, ketones, esters, and amides, were selected as halogen-bond acceptors. In the absence of strong hydrogen bonds, 14 out of 16 combinations of halogen-bond donors and acceptors could form cocrystals, whereby the supramolecular synthon C=O center dot center dot center dot X acts as the main interaction. Further, the geometric parameters of the C= O center dot center dot center dot X interaction were statistically revealed on the basis of the crystallographic database. The bifurcated interaction mode that has been observed in other halogen-bond synthons rarely occurs in the case of C=O center dot center dot center dot X. The robustness of C=O center dot center dot center dot X makes its application in crystal engineering possible and opens up new opportunities in designing multicomponent fluorescent materials, as indicated by multicolor emission of cocrystals D through C=O center dot center dot center dot X interactions.
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