Issue 12, 2002
From the journal:

Photochemical & Photobiological Sciences

Photochemical transformations of 2,2′-(1,2-phenylenedivinylene)dipyrroles

Nikola Basarić,a   Željko Marinić,b   Aleksandar Višnjevac,c   Biserka Kojić-Prodić,c   Axel G. Griesbeckd  and  Marija Šindler-Kulyk*a  

* Corresponding authors

a Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev Trg 19, HR-10000 Zagreb, Croatia
E-mail: marija.sindler@pierre.fkit.hr

b NMR Center, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia

c Department of Physical Chemistry, Ruđer Bošković Institute, P. O. Box 180, HR-10002 Zagreb, Croatia

d Institute of Organic Chemistry, University of Cologne, Greinstr. 4 D-50939 Köln, Germany

Abstract

The photochemistry of 2,2′-(1,2-phenylenedivinylene)dipyrroles (4a,b) has been investigated under various conditions. After excitation of the starting material, an electron transfer followed by hydrogen transfer and radical combination occurs giving 2-{[1-(2H-pyrrol-2-ylidene)methinyl]-2-indanyl}pyrrole (14) as the intermediate. The intermediate could not be isolated, but trapped by nucleophiles, like methanol and diethylamine, giving as addition products, new functionalised indanylpyrroles (9). Irradiation of 4a in the presence of triethylamine afforded the indanylidene-pyrroles 8.

Graphical abstract: Photochemical transformations of 2,2′-(1,2-phenylenedivinylene)dipyrroles

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Article information

DOI
https://doi.org/10.1039/B209127E
Article type
Paper
Submitted
19 Sep 2002
Accepted
28 Oct 2002
First published
20 Nov 2002

Photochem. Photobiol. Sci., 2002,1, 1017-1023

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Photochemical transformations of 2,2′-(1,2-phenylenedivinylene)dipyrroles

N. Basarić, Ž. Marinić, A. Višnjevac, B. Kojić-Prodić, A. G. Griesbeck and M. Šindler-Kulyk, Photochem. Photobiol. Sci., 2002, 1, 1017 DOI: 10.1039/B209127E

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