Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 4, Pages 1619-1626Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909401
Keywords
chirality; conjugation; macrocycles; nanotubes; photophysics
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Funding
- National Key Research and Development Program of China [2017YFA0402800]
- National Natural Science Foundation of China [21971229, 51772285]
- Zhejiang Provincial Natural Science Foundation [LR19B010001]
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Carbon nanotubes (CNTs) have unusual physical properties that are valuable for nanotechnology and electronics, but the chemical synthesis of chirality- and diameter-specific CNTs and pi-conjugated CNT segments is still a great challenge. Reported here are the selective syntheses, isolations, characterizations, and photophysical properties of two novel chiral conjugated macrocycles ([4]cyclo-2,6-anthracene; [4]CAn(2,6)), as (-)/(+)-(12,4) carbon nanotube segments. These conjugated macrocyclic molecules were obtained using a bottom-up assembly approach and subsequent reductive elimination reaction. The hoop-shaped molecules can be directly viewed by a STM technique. In addition, chiral enantiomers with (-)/(+) helicity of the [4]CAn(2,6) were successfully isolated by HPLC. The new tubular CNT segments exhibit large absorption and photoluminescence redshifts compared to the monomer unit. The carbon enantiomers are also observed to show strong circularly polarized luminescence (g(lum)approximate to 0.1). The results reported here expand the scope of materials design for bottom-up synthesis of chiral macrocycles and enrich existing knowledge of their optoelectronic properties.
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