Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives

Gendron, David, Gann, Eliot, Pattison, Katherine, Maasoumi, Fatemeh, McNeill, Christopher R., Watkins, Scott E., Burn, Paul L., Powell, Benjamin J. and Shaw, Paul E. (2014) Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives. Journal of Materials Chemistry C, 21 2: 4276-4288. doi:10.1039/c4tc00427b

Author Gendron, David
Gann, Eliot
Pattison, Katherine
Maasoumi, Fatemeh
McNeill, Christopher R.
Watkins, Scott E.
Burn, Paul L.
Powell, Benjamin J.
Shaw, Paul E.
Title Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives
Formatted title
Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives
Journal name Journal of Materials Chemistry C   Check publisher's open access policy
ISSN 2050-7526
Publication date 2014-06-07
Sub-type Article (original research)
DOI 10.1039/c4tc00427b
Open Access Status Not Open Access
Volume 21
Issue 2
Start page 4276
End page 4288
Total pages 13
Place of publication Cambridge, United Kingdom
Publisher R S C Publications
Language eng
Formatted abstract
The synthesis of three pyrrolo[3,2-b]pyrrole-1,4-dione (isoDPP) derivatives is described, namely 1,3,4,6-tetraphenylpyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione 2, 1,4-diphenyl-3,6-di(thiophen-2-yl)pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione 3, and 1,4-bis(4-(hexyloxy)phenyl)-3,6-di(thiophen-2-yl)pyrrolo[3,2-b]pyrrole-2,5(1H,4H)-dione 7 in which the molecular structures differ in the aromatic ring (phenyl or thiophene) attached to the nitrogen atom. Thin films of 2, 3, and 7 could be formed by evaporation under vacuum. In the case of 2 and 3 GIWAXS measurements showed that the film structural ordering was similar to that measured in single crystals. In contrast GIWAXS showed that 7 had features associated with liquid crystalline materials. Time dependent density functional theory (TDDFT) calculations predicted that the transition between the lowest energy singlet excitation (S1) and the ground state (S0) would be optically forbidden due to the centrosymmetric geometries of compounds. Photophysical measurements showed that the compounds were weakly luminescent, with low radiative rates in solution of order 106 s−1, which are consistent with the TDDFT predictions. Furthermore, photoinduced absorption (PIA) spectroscopy showed that there is a long-lived low energy state, which has been assigned as a triplet and provides a further non-radiative decay pathway for the excited state.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

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Created: Fri, 06 Jun 2014, 19:50:26 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences