Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 11, Pages 3069-3076Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201304541
Keywords
crystal engineering; fluorescence; host-guest systems; hydrogen bonds; immobilization
Categories
Funding
- Japan Society for the Promotion of Science (JSPS) for Young Scientists
- Ministry of Education, Culture, Sports, Science and Technology (MEXT), Japan [22685014, 24108723, 24655124]
- Grants-in-Aid for Scientific Research [24655124, 25288048, 22685014, 25288036, 24108723] Funding Source: KAKEN
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A host framework for inclusion of various guest molecules was investigated by preparation of inclusion crystals of 1,8-bis(4-aminophenyl)anthracene (1,8-BAPA) with organic solvents. X-ray crystallographic analysis revealed construction of the same inclusion space incorporating 1,8-BAPA and eight guest molecules including both non-polar (benzene) and polar guests (N,N-dimethylformamide, DMF). Fluorescence efficiencies varied depending on guest molecule polarity; DMF inclusion crystals exhibited the highest fluorescence intensity (phi(F)=0.40), four times as high as that of a benzene inclusion crystal (phi(F)=0.10). According to systematic investigations of inclusion phenomena, strong host-guest interactions and filling of the inclusion space led to a high fluorescence intensity. Temperature-dependent fluorescence spectral measurements revealed these factors effectively immobilised the host framework. Although hydrogen bonding commonly decreases fluorescence intensity, the present study demonstrated that such strong interactions provide excellent conditions for fluorescence enhancement. Thus, this remarkable behaviour has potential application toward sensing of highly polar molecules, such as biogenic compounds.
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