Charge and Spin Transport in an Organic Molecular Square

Yilei Wu, Siva Krishna Mohan Nalluri, Ryan M. Young, Matthew D. Krzyaniak, Eric A. Margulies, J. Fraser Stoddart, Michael R Wasielewski

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Understanding electronic communication among multiple chromophoric and redox units requires construction of well-defined molecular architectures. Herein, we report the modular synthesis of a shape-persistent chiral organic square composed of four naphthalene-1,8:4,5-bis(dicarboximide) (NDI) sides and four trans-1,2-cyclohexanediamine corners. Single crystal X-ray diffraction reveals some distortion of the cyclohexane chair conformation in the solid state. Analysis of the packing of the molecular squares reveals the formation of highly ordered, one-dimensional tubular superstructures, held together by means of multiple [C-H⋯O=C] hydrogen-bonding interactions. Steady-state and time-resolved electronic spectroscopies show strong excited-state interactions in both the singlet and triplet manifolds. Electron paramagnetic resonance (EPR) and electron-nuclear double resonance (ENDOR) spectroscopies on the monoreduced state reveal electron sharing between all four NDI subunits comprising the molecular square.

Original languageEnglish
Pages (from-to)11971-11977
Number of pages7
JournalAngewandte Chemie - International Edition
Volume54
Issue number41
DOIs
Publication statusPublished - Oct 1 2015

Fingerprint

Spectroscopy
Naphthalene
Cyclohexane
Excited states
Electron energy levels
Paramagnetic resonance
Conformations
Hydrogen bonds
Single crystals
X ray diffraction
Electrons
Communication
Oxidation-Reduction
1,2-cyclohexanediamine
naphthalene-1,8:4,5-bis(dicarboximide)

Keywords

  • electron transport
  • hydrogen bonding
  • molecular electronics
  • molecular squares
  • organic semiconductors

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Wu, Y., Nalluri, S. K. M., Young, R. M., Krzyaniak, M. D., Margulies, E. A., Stoddart, J. F., & Wasielewski, M. R. (2015). Charge and Spin Transport in an Organic Molecular Square. Angewandte Chemie - International Edition, 54(41), 11971-11977. https://doi.org/10.1002/anie.201504576

Charge and Spin Transport in an Organic Molecular Square. / Wu, Yilei; Nalluri, Siva Krishna Mohan; Young, Ryan M.; Krzyaniak, Matthew D.; Margulies, Eric A.; Stoddart, J. Fraser; Wasielewski, Michael R.

In: Angewandte Chemie - International Edition, Vol. 54, No. 41, 01.10.2015, p. 11971-11977.

Research output: Contribution to journalArticle

Wu, Y, Nalluri, SKM, Young, RM, Krzyaniak, MD, Margulies, EA, Stoddart, JF & Wasielewski, MR 2015, 'Charge and Spin Transport in an Organic Molecular Square', Angewandte Chemie - International Edition, vol. 54, no. 41, pp. 11971-11977. https://doi.org/10.1002/anie.201504576
Wu Y, Nalluri SKM, Young RM, Krzyaniak MD, Margulies EA, Stoddart JF et al. Charge and Spin Transport in an Organic Molecular Square. Angewandte Chemie - International Edition. 2015 Oct 1;54(41):11971-11977. https://doi.org/10.1002/anie.201504576
Wu, Yilei ; Nalluri, Siva Krishna Mohan ; Young, Ryan M. ; Krzyaniak, Matthew D. ; Margulies, Eric A. ; Stoddart, J. Fraser ; Wasielewski, Michael R. / Charge and Spin Transport in an Organic Molecular Square. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 41. pp. 11971-11977.
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