Full Paper

Hydrogen Bonding Induced Supramolecular Self-Assembly of Linear Doubly Discotic Triad Supermolecules

  1. Jianjun Miao1,
  2. Lei Zhu Prof.1,2

Article first published online: 21 MAY 2010

DOI: 10.1002/asia.201000017

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Volume 5, Issue 7, pages 1634–1641, July 5, 2010

Additional Information

How to Cite

Miao, J. and Zhu, L. (2010), Hydrogen Bonding Induced Supramolecular Self-Assembly of Linear Doubly Discotic Triad Supermolecules. Chem. Asian J., 5: 1634–1641. doi: 10.1002/asia.201000017

Author Information

  1. 1

    Polymer Program, Institute of Materials Science and Department of Chemical, Materials and Biomolecular Engineering, University of Connecticut, Storrs, Connecticut 06269-3136 (USA), Fax: (+1) 216-368-4202

  2. 2

    Department Department of Macromolecular Science and Engineering, Case Western Reserve University, Cleveland, Ohio 44106-7202 (USA)

Publication History

  1. Issue published online: 1 JUL 2010
  2. Article first published online: 21 MAY 2010
  3. Manuscript Received: 8 JAN 2010

Funded by

  • NSF
  • DuPont
  • Department of Energy

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Keywords:

  • hydrogen-bonding;
  • porphyrins;
  • self-assembly;
  • supermolecular chemistry;
  • triphenylene

Abstract

A series of linear doubly discotic triad supermolecules based on a porphyrin (P) core and two triphenylene (Tp) arms linked by amide bonds are synthesized. The samples are denoted as P(Tp)2. Hydrogen bonding along the P stacks is the primary driving force for the supramolecular self-assembly of P(Tp)2 triad supermolecules. Meanwhile, the degree of coupling between P and Tp disks also plays an important role. For samples with the spacer lengths longer than or similar to the alkyl chain lengths in the Tp arms, P and Tp are decoupled to a large degree. This decoupling result in non-uniform tilt angles for P and Tp disks along both the a- and c-axes. Therefore, large unit cells are observed with eight P(Tp)2 supermolecules per cell. For a sample with the spacer length much shorter than the alkyl chains in the Tp arms, P and Tp are strongly coupled. Therefore, both P and Tp have uniform tilt angles along the a- and c-axes. A small unit cell is obtained with only one P(Tp)2 supermolecule per cell.

Featured Compounds

Compound 1
Molecular Weight:2214.97
Molecular Formula:C144H176N6O14
InChIKey:AQGMSVLXFMKKCQ-XAFSNOSVSA-N
View compound in article | Full details | Search this compound
Compound 2
Molecular Weight:2327.1826
Molecular Formula:C152H192N6O14
InChIKey:ADXQKCPMUZFUHV-JCXATAEWSA-N
View compound in article | Full details | Search this compound
Compound 3
Molecular Weight:3196.8306
Molecular Formula:C214H316N6O14
InChIKey:LIBRGDDSMABIBZ-HNCNGDOKSA-N
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Compound 4
Molecular Weight:3309.0432
Molecular Formula:C222H332N6O14
InChIKey:CLDHRGJMCOMQOB-NDLLMHMPSA-N
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View Full Article with Supporting Information (HTML) Get PDF (553K)