Assembling phenomena of calix[4]hydroquinone nanotube bundles by one-dimensional short hydrogen bonding and displaced π-π stacking

Kwang S. Kim, Seung Bum Suh, Jong Chan Kim, Byung Hee Hong, Eun Cheol Lee, Sunggoo Yun, P. Tarakeshwar, Jin Yong Lee, Yukyung Kim, Hyejae Ihm, Heon Gon Kim, Jung Woo Lee, Jung Kyung Kim, Han Myoung Lee, Dongwook Kim, Chunzhi Cui, Suk Joo Youn, Hae Yong Chung, Hyuck Soon Choi, Chi Wan LeeSeung Joo Cho, Sukmin Jeong, Jun Hyung Cho

Research output: Contribution to journalArticlepeer-review

114 Scopus citations


Using the computer-aided molecular design approach, we recently reported the synthesis of calix[4]hydroquinone (CHQ) nanotube arrays self-assembled with infinitely long one-dimensional (1-D) short hydrogen bonds (H-bonds) and aromatic - aromatic interactions. Here, we assess various calculation methods employed for both the design of the CHQ nanotubes and the study of their assembly process. Our calculations include ab initio and density functional theories and first principles calculations using ultrasoft pseudopotential plane wave methods. The assembly phenomena predicted prior to the synthesis of the nanotubes and details of the refined structure and electronic properties obtained after the experimental characterization of the nanotube crystal are reported. For better characterization of intriguing 1-D short H-bonds and exemplary displaced π - π stacks, the X-ray structures have been further refined with samples grown in different solvent conditions. Since X-ray structures do not contain the positions of H atoms, it is necessary to analyze the system using quantum theoretical calculations. The competition between H-bonding and displaced π - π stacking in the assembling process has been clarified. The IR spectroscopic features and NMR chemical shifts of 1-D short H-bonds have been investigated both experimentally and theoretically. The dissection of the two most important interaction components leading to self-assembly processes would help design new functional materials and nanomaterials.

Original languageEnglish (US)
Pages (from-to)14268-14279
Number of pages12
JournalJournal of the American Chemical Society
Issue number47
StatePublished - Nov 27 2002
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry


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