-Carbon-carbon double bond engineering in diazaphosphepines: A pathway to modulate the chemical and electronic structures of heteropines

Yi Ren, Melda Sezen, Fang Guo, Frieder Jäkle, Yueh Lin Loo

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

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]-CC 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.

Original languageEnglish (US)
Pages (from-to)4211-4219
Number of pages9
JournalChemical Science
Volume7
Issue number7
DOIs
StatePublished - 2016

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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