Issue 21, 2014

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
04 Mar 2014
Accepted
01 Apr 2014
First published
23 Apr 2014

J. Mater. Chem. C, 2014,2, 4276-4288

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements