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Issue 5, 2010
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Optoelectronically mismatched oligophenylethynyl-naphthalenediimide SHJ architectures

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The objective of this study was to evaluate the possibility of photoinduced stack/rod electron transfer in surface “zipper” architectures composed of stacks of blue (B) naphthalenediimides (NDIs) along strings of oligophenylethynyl (OPE) rods. The synthesis and characterization of anionic and cationic multichromophoric OPE-B systems are reported. Absorption spectra suggest that in OPE-B systems, planarity and thus absorption and conductivity of the OPE can possibly be modulated by intramolecular stacking of the surrounding NDIs, although interfering contributions from aggregation remain to be differentiated. Among surface architectures constructed with OPE-B and POP-B systems by zipper and layer-by-layer (LBL) assembly, photocurrents generated by OPE-B zippers exhibit the best critical thickness and fill factors. These findings confirm the existence and functional relevance of topologically matching zipper architectures. In OPE-B zippers, OPEs generate much more photocurrent than the blue NDIs. Ultrafast electron transfer from OPEs to NDIs accounts for these photocurrents, providing wavelength-controlled access to rod–stack charge separation, and thus to formal supramolecular n/p-heterojunctions (SHJs). NDI excitation is not followed by the complementary hole transfer to the OPE rod. Scaffolds with higher HOMOs will be needed to integrate blue NDIs into SHJ photosystems.

Graphical abstract: Optoelectronically mismatched oligophenylethynyl-naphthalenediimide SHJ architectures

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Publication details

The article was received on 20 Aug 2009, accepted on 14 Dec 2009 and first published on 18 Jan 2010

Article type: Paper
DOI: 10.1039/B917188F
Citation: Org. Biomol. Chem., 2010,8, 1052-1057
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    Optoelectronically mismatched oligophenylethynyl-naphthalenediimide SHJ architectures

    S. Maity, R. Bhosale, N. Banerji, E. Vauthey, N. Sakai and S. Matile, Org. Biomol. Chem., 2010, 8, 1052
    DOI: 10.1039/B917188F

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