Lock-arm supramolecular ordering: A molecular construction set for cocrystallizing organic charge transfer complexes

Anthea K. Blackburn, Andrew C H Sue, Alexander K. Shveyd, Dennis Cao, Alok Tayi, Ashwin Narayanan, Brian S. Rolczynski, Jodi M. Szarko, Ozgur A. Bozdemir, Rie Wakabayashi, Jessica A. Lehrman, Bart Kahr, Lin X. Chen, Majed S. Nassar, Samuel I Stupp, J. Fraser Stoddart

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Organic charge transfer cocrystals are inexpensive, modular, and solution-processable materials that are able, in some instances, to exhibit properties such as optical nonlinearity, (semi)conductivity, ferroelectricity, and magnetism. Although the properties of these cocrystals have been investigated for decades, the principal challenge that researchers face currently is to devise an efficient approach which allows for the growth of high-quality crystalline materials, in anticipation of a host of different technological applications. The research reported here introduces an innovative design, termed LASO-lock-arm supramolecular ordering-in the form of a modular approach for the development of responsive organic cocrystals. The strategy relies on the use of aromatic electronic donor and acceptor building blocks, carrying complementary rigid and flexible arms, capable of forming hydrogen bonds to amplify the cocrystallization processes. The cooperativity of charge transfer and hydrogen-bonding interactions between the building blocks leads to binary cocrystals that have alternating donors and acceptors extending in one and two dimensions sustained by an intricate network of hydrogen bonds. A variety of air-stable, mechanically robust, centimeter-long, organic charge transfer cocrystals have been grown by liquid-liquid diffusion under ambient conditions inside 72 h. These cocrystals are of considerable interest because of their remarkable size and stability and the promise they hold when it comes to fabricating the next generation of innovative electronic and photonic devices.

Original languageEnglish
Pages (from-to)17224-17235
Number of pages12
JournalJournal of the American Chemical Society
Volume136
Issue number49
DOIs
Publication statusPublished - Dec 10 2014

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Charge transfer
Hydrogen
Hydrogen bonds
Optics and Photonics
Hydrogen Bonding
Diffusion in liquids
Ferroelectricity
Photonic devices
Air
Research Personnel
Magnetism
Equipment and Supplies
Growth
Research
Crystalline materials
Liquids

ASJC Scopus subject areas

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

Cite this

Blackburn, A. K., Sue, A. C. H., Shveyd, A. K., Cao, D., Tayi, A., Narayanan, A., ... Stoddart, J. F. (2014). Lock-arm supramolecular ordering: A molecular construction set for cocrystallizing organic charge transfer complexes. Journal of the American Chemical Society, 136(49), 17224-17235. https://doi.org/10.1021/ja509442t

Lock-arm supramolecular ordering : A molecular construction set for cocrystallizing organic charge transfer complexes. / Blackburn, Anthea K.; Sue, Andrew C H; Shveyd, Alexander K.; Cao, Dennis; Tayi, Alok; Narayanan, Ashwin; Rolczynski, Brian S.; Szarko, Jodi M.; Bozdemir, Ozgur A.; Wakabayashi, Rie; Lehrman, Jessica A.; Kahr, Bart; Chen, Lin X.; Nassar, Majed S.; Stupp, Samuel I; Stoddart, J. Fraser.

In: Journal of the American Chemical Society, Vol. 136, No. 49, 10.12.2014, p. 17224-17235.

Research output: Contribution to journalArticle

Blackburn, AK, Sue, ACH, Shveyd, AK, Cao, D, Tayi, A, Narayanan, A, Rolczynski, BS, Szarko, JM, Bozdemir, OA, Wakabayashi, R, Lehrman, JA, Kahr, B, Chen, LX, Nassar, MS, Stupp, SI & Stoddart, JF 2014, 'Lock-arm supramolecular ordering: A molecular construction set for cocrystallizing organic charge transfer complexes', Journal of the American Chemical Society, vol. 136, no. 49, pp. 17224-17235. https://doi.org/10.1021/ja509442t
Blackburn, Anthea K. ; Sue, Andrew C H ; Shveyd, Alexander K. ; Cao, Dennis ; Tayi, Alok ; Narayanan, Ashwin ; Rolczynski, Brian S. ; Szarko, Jodi M. ; Bozdemir, Ozgur A. ; Wakabayashi, Rie ; Lehrman, Jessica A. ; Kahr, Bart ; Chen, Lin X. ; Nassar, Majed S. ; Stupp, Samuel I ; Stoddart, J. Fraser. / Lock-arm supramolecular ordering : A molecular construction set for cocrystallizing organic charge transfer complexes. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 49. pp. 17224-17235.
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