Recent Developments in Phosphole‐Containing Oligo‐ and Polythiophene Materials

Hobbs, Matthew G.; Baumgartner, Thomas

doi:10.1002/chin.200744231

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a result, phosphole exhibits very low aromaticity ( Egan, et al, 1971 ; Epitotis, et al, 1976 ; Mathey, et al, 1988 ; Cyrañski, et al, 2002 ; Chesnut, et al, 2007 ). Because of such a structural feature, conjugated molecules involving phosphole and its analogs have recently attracted attention in the field of organic semiconductor development, including light-emitting and electronic materials ( Hay, et al, 2001 ; Hissler, et al, 2003 ; Baumgartner, et al, 2004 ; Su, et al, 2006 ; Hobbs, et al, 2007 ; Crassous, et al, 2008 ; Matano, et al, 2009 ; Ren, et al, 2012 ). Despite their promising material properties, synthetic examples of five-membered ring heterocyclic compounds containing phosphorus are rather limited.…”

Section: Introductionmentioning

confidence: 99%

Practical synthesis of 1,3-benzoazaphosphole analogues

et al. 2023

View full text Add to dashboard Cite

Despite the promising pharmacological activity and material properties of five-membered heterocyclic compounds containing phosphorus and nitrogen, synthetic examples of them have been rather limited due to the instability of phosphorus toward air and water. In this study, 1,3-benzoazaphosphol analogues were selected as target molecules, and various synthetic routes were examined to establish a fundamental technology for the introduction of phosphorus groups into aromatic rings and formation of five-membered rings containing phosphorus and nitrogen by cyclization. As a result, we found that 2-aminophenyl(phenyl)phosphine is an extremely promising synthetic intermediate with high stability and easy handling. Furthermore, 2-methyl-3-phenyl-2,3-dihydro-1H-benzo[d][1,3]azaphosphole and 3-phenyl-2,3-dihydro-1H-benzo[d][1,3]azaphosphole-2-thione as synthetically useful 1,3-benzoazaphosphol analogues were successfully synthesized by using 2-aminophenyl(phenyl)phosphine as a key intermediate.

show abstract