Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 26, Pages 6323-6329Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605598
Keywords
aggregation-induced emission; chirality; conjugation; luminescence; paracyclophanes
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [24685018]
- Japan Society for the Promotion of Science for Young Scientists [14J02514]
- Grants-in-Aid for Scientific Research [14J02514, 24685018, 17H05165] Funding Source: KAKEN
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Optically active phenylethene dimers based on a planar chiral 4,7,12,15-tetrasubstituted [2.2]paracyclophane were synthesized. We succeeded in controlling the molecular motion by binding luminophores in close proximity with the [2.2]paracyclophane scaffold. For example, aggregation-induced emission (AIE)-active luminophores were converted to show intense photoluminescence (PL) even in a diluted solution at room temperature and the resulting compound worked as a single-molecule thermoresponsible material around room temperature. Because of the AIE-active unit, the molecular motion could be easily activated by heating, leading to variable and reversible PL intensity. Furthermore, the -conjugated systems with the planar chirality of 4,7,12,15-tetrasubstituted [2.2]paracyclophane provided excellent characteristics on circular dichroism (CD) and circularly polarized luminescence (CPL). The obtained dimers showed high CPL performances both in a diluted solution and in an aggregation state. We succeeded in proving that simple molecular designs composed of only carbon and hydrogen atoms could create versatile optical functionalities.
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