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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE (Open Access)

Some Products from C=O Condensations of Quinacridones

Anthony S. R. Chesman https://orcid.org/0000-0002-1807-4468 A B C and Andris J. Liepa A
+ Author Affiliations
- Author Affiliations

A CSIRO Manufacturing, Jerry Price Laboratory, Clayton, Vic. 3168, Australia.

B Melbourne Centre of Nanofabrication, Clayton, Vic. 3168, Australia.

C Corresponding author. Email: anthony.chesman@csiro.au

Australian Journal of Chemistry 74(2) 111-124 https://doi.org/10.1071/CH20109
Submitted: 7 April 2020  Accepted: 6 May 2020   Published: 25 August 2020

Journal Compilation © CSIRO 2021 Open Access CC BY

Abstract

Quinacridone chemistry has been developed which provides a source of new compounds that have potential application in organic photovoltaic (OPV) devices. Phosphoryl chloride is used for the conversion of carbonyl groups in N,N′-dialkylquinacridones, generating reactive intermediates that enable selective condensation with either one or two nucleophilic molecules under mild conditions.


References

[1]  P. M. Beaujuge, J. M. J. Frechet, J. Am. Chem. Soc. 2011, 133, 20009.
         | Crossref | GoogleScholarGoogle Scholar | 21999757PubMed |

[2]  M. Lloyd, J. Anthony, G. Malliaras, Mater. Today 2007, 10, 34.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  J. Roncali, Acc. Chem. Res. 2009, 42, 1719.
         | Crossref | GoogleScholarGoogle Scholar | 19580313PubMed |

[4]  Z. He, B. Xiao, F. Liu, H. Wu, Y. Yang, S. Xiao, C. Wang, T. P. Russell, Y. Cao, Nat. Photonics 2015, 9, 174.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  J. J. Chen, T. L. Chen, B. Kim, D. A. Poulsen, J. L. Mynar, J. M. Frechet, B. Ma, ACS Appl. Mater. Interfaces 2010, 2, 2679.
         | Crossref | GoogleScholarGoogle Scholar | 20804141PubMed |

[6]  I. Javed, A. Khurshid, M. N. Arshad, Y. Wang, New J. Chem. 2014, 38, 752.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  S. De Feyter, A. Gesquière, F. C. De Schryver, U. Keller, K. Müllen, Chem. Mater. 2002, 14, 989.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  T. Zhou, T. Jia, B. Kang, F. Li, M. Fahlman, Y. Wang, Adv. Energy Mater. 2011, 1, 431.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  T. Takeda, H. Sugihara, Y. Suzuki, J. Kawamata, T. Akutagawa, J. Org. Chem. 2014, 79, 9669.
         | Crossref | GoogleScholarGoogle Scholar | 25254634PubMed |

[10]  W. Chen, L. Weiping, J. Lv, J. Han, Y. Chen, T. Jia, L. Tao, Y. Wang, J. Mater. Chem. A 2016, 4, 2169.
         | Crossref | GoogleScholarGoogle Scholar |

[11]  I. Javed, T. Zhou, F. Muhammad, J. Guo, H. Zhang, Y. Wang, Langmuir 2012, 28, 1439.
         | Crossref | GoogleScholarGoogle Scholar | 22149176PubMed |

[12]  W. Chen, K. Tian, X. Song, Z. Zhang, K. Ye, G. Yu, Y. Wang, Org. Lett. 2015, 17, 6146.
         | Crossref | GoogleScholarGoogle Scholar | 26605431PubMed |

[13]  D. T. Mowry, J. Am. Chem. Soc. 1945, 67, 1050.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  J. Jia, Y. Li, W. Wang, C. Luo, L. Han, Y. Li, J. Gao, Dyes Pigm. 2017, 146, 251.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  R. M. Fekry, H. A. El-Sayed, M. G. Assy, A. Shalby, A. S. Mohamed, Organic Chem. Curr. Res. 2016, 5, 171.
         | Crossref | GoogleScholarGoogle Scholar |

[16]  Y. Zhu, L. Yi, M. Q. Yao, X. Li, Org. Chem. Front. 2016, 3, 709.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  V. Kundi, P. P. Thankachan, J. Phys. Chem. A 2016, 120, 2757.
         | Crossref | GoogleScholarGoogle Scholar | 27054876PubMed |

[18]  A. M. Asiri, Appl. Organomet. Chem. 2001, 15, 907.
         | Crossref | GoogleScholarGoogle Scholar |

[19]  F. Schwartz, L. F. Worrell, J. N. Delgado, J. Pharm. Sci. 1967, 56, 80.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  A. Bello, L. Cheng, J. Griffiths, J. Chem. Soc., Perkin Trans. 2 1987, 6, 815.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  J. B. Dorsch, S. M. McElvain, J. Am. Chem. Soc. 1932, 54, 2960.
         | Crossref | GoogleScholarGoogle Scholar |

[22]  G. M. Sheldrick, Acta Crystallogr. 2008, A64, 112.
         | Crossref | GoogleScholarGoogle Scholar |

[23]  T. M. McPhillips, S. E. McPhillips, H. J. Chiu, A. E. Cohen, A. M. Deacon, P. J. Ellis, E. Garman, A. Gonzalez, N. K. Sauter, R. P. Phizackerley, S. M. Soltis, P. Kuhn, J. Synchrotron Radiat. 2002, 9, 401.
         | Crossref | GoogleScholarGoogle Scholar | 12409628PubMed |

[24]  W. Kabsch, J. Appl. Cryst. 1993, 26, 795.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  L. J. Barbour, J. Supramol. Chem. 2001, 1, 189.
         | Crossref | GoogleScholarGoogle Scholar |