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Issue 7, 2016
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[d]-Carbon–carbon double bond engineering in diazaphosphepines: a pathway to modulate the chemical and electronic structures of heteropines

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Abstract

We have designed and synthesized the first examples of 7-membered diazaphosphepines using phosphorus–amine (P–N) chemistry. Different from previous functional protocols of heteropines, the installation of π-conjugated substituents having diverse chemistries at the [d]-C[double bond, length as m-dash]C double bond position of heteropine core allows us to effectively control the chemical and electronic structures in both the ground and excited states of these diazaphosphepines. This functionalization has led to a diverse set of crystal structures, which has in turn provided access to rich photophysical and redox properties. Of particular interest is the evidence for planar π-conjugated backbone in our non-aromatic heteropine and twisted intramolecular charge transfer, which have never been reported for heteropines. The introduction of electron-accepting substituents at [d]-position of diazaphosphepines results in heteropines that are more electron deficient than any heteropine reported to-date. As proof of concept, we have fabricated organic solar cells with heteropines as non-fullerene acceptors.

Graphical abstract: [d]-Carbon–carbon double bond engineering in diazaphosphepines: a pathway to modulate the chemical and electronic structures of heteropines

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Publication details

The article was received on 02 Feb 2016, accepted on 15 Mar 2016 and first published on 15 Mar 2016


Article type: Edge Article
DOI: 10.1039/C6SC00519E
Citation: Chem. Sci., 2016,7, 4211-4219
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    [d]-Carbon–carbon double bond engineering in diazaphosphepines: a pathway to modulate the chemical and electronic structures of heteropines

    Y. Ren, M. Sezen, F. Guo, F. Jäkle and Y. Loo, Chem. Sci., 2016, 7, 4211
    DOI: 10.1039/C6SC00519E

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