Skip to main content
SpringerLink
Log in

On the chemistry of pyrrole pigments, XCVII: Synthesis, stereochemistry, and solvatochromic effects of a 1-(dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-1-propene

Zur Chemie von Pyrrolpigmenten, 97. Mitt.: Synthese, Stereochemie und Solvatochromer Effekt eines 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-yliden)-1-propens

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

By condensing a dipyrrinon-9-yl-acrolein with a dipyrrinone unsubstituted in position 9, an unsymmetricb-vinylogous verdinoid pigment was prepared. The configuration of this molecule was elucidated by means of 2D1H NMR experiments to be (4Z,10E,12Z,17Z) in solutions of chloroform and dimethylsulfoxide, and its conformation was derived to be 5syn,9syn,11anti,16syn. The pronounced solvatochromic effect of this molecule with a cyclic helical geometry could be explained by solvent induced conformational changes.

Zusammenfassung

Durch Kondensation eines Dipyrrinon-9-yl-acroleins mit einem in Position 9 unsubstituierten Dipyrrinon wurde ein unsymmetrischesb-vinyloges verdinoides Pigment dargestellt. Die Konfiguration dieses Moleküls wurde mit Hilfe von 2D-1H-NMR-Experimenten in Lösungen von und Dimethylsulfoxid als (4Z,10E,12Z,17Z) abgeleitet; seine Konformation konnte zu 5syn,9syn,11anti,16syn festgelegt werden. Die ausgeprägte Solvatochromie dieses Moleküls mit cyclisch helikaler Geometrie konnte auf solvensinduzierte konformative Veränderungen zurückgeführt werden.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Part XCVI: Chen Q-Q, Falk H (1996) Monatsh Chem127: 69

    Google Scholar 

  2. Chen Q-Q, Falk H (1995) Monatsh Chem126: in press

  3. Gosman M, Franck B (1986) Angew Chem98: 1107, (1986) Angew Chem Int Ed Engl25: 1100; Franck B, Gosmann M (1988) DOS 3635820 (Vinyloge Porphyrine) BASF AG, Chem Abstr109: 94748; Beckman VS, Wessel T, Franck B, Hönle W, Borrmann H, Schnering HGV (1990) Angew Chem102: 1439

    Google Scholar 

  4. Falk H (1989) The chemistry of linear oligopyrroles and bile pigments. Springer, Wien New York

    Google Scholar 

  5. PCMODEL v 5.0, (1994) Serena software, Bloomington, USA

  6. Albert A, Serjeant EP (1984) The determination of ionization constants. Chapman & Hall, London

    Google Scholar 

  7. Ball & Stick Program, Müller N, Falk A (1993) Cherwell Scientific

  8. Rowold A, MacDonald SF (1978) Can J Chem56: 1907

    Google Scholar 

  9. Atkinson JH, Atkinson RS, Johnson AW (1964) J Chem Soc1964: 5999; Byun YS, Lightner DA (1991) J Org Chem56: 6027; Ichimura K, Ichikawa S, Imamura K (1976) Bull Chem Soc Jap49: 1157

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Chemie, Johannes-Kepler Universität Linz, A-4040, Linz, Austria

    H. Falk, Q. -Q. Chen & R. Micura

Authors
  1. H. Falk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Q. -Q. Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. Micura
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Falk, H., Chen, Q.Q. & Micura, R. On the chemistry of pyrrole pigments, XCVII: Synthesis, stereochemistry, and solvatochromic effects of a 1-(dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-1-propene. Monatsh Chem 127, 77–83 (1996). https://doi.org/10.1007/BF00807411

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00807411

Keywords

Search

Navigation