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 language | English (US) |
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Pages (from-to) | 11971-11977 |
Number of pages | 7 |
Journal | Angewandte Chemie - International Edition |
Volume | 54 |
Issue number | 41 |
DOIs | |
State | Published - Oct 1 2015 |
Keywords
- electron transport
- hydrogen bonding
- molecular electronics
- molecular squares
- organic semiconductors
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
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CCDC 1041583: Experimental Crystal Structure Determination
Wu, Y. (Creator), Nalluri, S. K. M. (Creator), Young, R. M. (Creator), Krzyaniak, M. D. (Creator), Margulies, E. A. (Creator), Stoddart, J. F. (Creator) & Wasielewski, M. R. (Creator), Cambridge Crystallographic Data Centre, 2015
DOI: 10.5517/cc13yvgc, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc13yvgc&sid=DataCite
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