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Issue 21, 2014
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Synthesis and properties of pyrrolo[3,2-b]pyrrole-1,4-diones (isoDPP) derivatives

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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 sāˆ’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.

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

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Publication details

The article was received on 04 Mar 2014, accepted on 01 Apr 2014 and first published on 23 Apr 2014


Article type: Paper
DOI: 10.1039/C4TC00427B
Citation: J. Mater. Chem. C, 2014,2, 4276-4288

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

    D. Gendron, E. Gann, K. Pattison, F. Maasoumi, C. R. McNeill, S. E. Watkins, P. L. Burn, B. J. Powell and P. E. Shaw, J. Mater. Chem. C, 2014, 2, 4276
    DOI: 10.1039/C4TC00427B

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