A family of heterocyclic naphthalene diimide (NDI) analogues

comparing parent isoquinoline diimides and phthalazine diimides with NDI

Alberto Insuasty, Serena Carrara, Linjing Tang, Craig Forsyth, Conor F. Hogan, Christopher R. McNeill, Steven J. Langford

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Parent isoquinoline diimide (IQDI) and phthalazine diimide (PTDI), as two new heterocyclic analogues of naphthalene diimides (NDIs), have been synthesized through an oxidative strategy in 35–79 % yield. X-ray crystallography has been used to support the formation of IQDI, which also show fluorescence quantum yields of 3.5 %. The electrochemical and electrical properties of these molecules have been studied. The electrochemical results show an interesting trend in first reduction potential PTDI<IQDI<NDI and 0.1 eV changes in the optical band gap (Eg) leading to the trend IQDI<NDI<PTDI, as supported by DFT calculations. While initial top gate OFET devices yield charge mobilities less than NDIs, the basis of this study intimates that IQDIs and PTDIs hold promise for applications commensurate with NDIs.

Original languageEnglish
Pages (from-to)1638-1642
Number of pages5
JournalChemPlusChem
Volume84
Issue number10
DOIs
Publication statusPublished - Oct 2019

Keywords

  • heterocycles
  • isoquinoline diimides
  • OFET devices
  • photophysics
  • phthalazine diimides

Cite this

Insuasty, Alberto ; Carrara, Serena ; Tang, Linjing ; Forsyth, Craig ; Hogan, Conor F. ; McNeill, Christopher R. ; Langford, Steven J. / A family of heterocyclic naphthalene diimide (NDI) analogues : comparing parent isoquinoline diimides and phthalazine diimides with NDI. In: ChemPlusChem. 2019 ; Vol. 84, No. 10. pp. 1638-1642.
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title = "A family of heterocyclic naphthalene diimide (NDI) analogues: comparing parent isoquinoline diimides and phthalazine diimides with NDI",
abstract = "Parent isoquinoline diimide (IQDI) and phthalazine diimide (PTDI), as two new heterocyclic analogues of naphthalene diimides (NDIs), have been synthesized through an oxidative strategy in 35–79 {\%} yield. X-ray crystallography has been used to support the formation of IQDI, which also show fluorescence quantum yields of 3.5 {\%}. The electrochemical and electrical properties of these molecules have been studied. The electrochemical results show an interesting trend in first reduction potential PTDI<IQDI<NDI and 0.1 eV changes in the optical band gap (Eg) leading to the trend IQDI<NDI<PTDI, as supported by DFT calculations. While initial top gate OFET devices yield charge mobilities less than NDIs, the basis of this study intimates that IQDIs and PTDIs hold promise for applications commensurate with NDIs.",
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A family of heterocyclic naphthalene diimide (NDI) analogues : comparing parent isoquinoline diimides and phthalazine diimides with NDI. / Insuasty, Alberto; Carrara, Serena; Tang, Linjing; Forsyth, Craig; Hogan, Conor F.; McNeill, Christopher R.; Langford, Steven J.

In: ChemPlusChem, Vol. 84, No. 10, 10.2019, p. 1638-1642.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - A family of heterocyclic naphthalene diimide (NDI) analogues

T2 - comparing parent isoquinoline diimides and phthalazine diimides with NDI

AU - Insuasty, Alberto

AU - Carrara, Serena

AU - Tang, Linjing

AU - Forsyth, Craig

AU - Hogan, Conor F.

AU - McNeill, Christopher R.

AU - Langford, Steven J.

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