Issue 6, 2016

Tunable and highly efficient light-harvesting antenna systems based on 1,7-perylene-3,4,9,10-tetracarboxylic acid derivatives

Abstract

We report the synthesis and excited-state dynamics of a series of five bichromophoric light-harvesting antenna systems, which are capable of efficient harvesting of solar energy in the spectral range of 350–580 nm. These antenna systems have been synthesized in a modular fashion by the covalent attachment of blue light absorbing naphthalene monoimide energy donors (D1, D2, and D3) to green light absorbing perylene-3,4,9,10-tetracarboxylic acid derived energy acceptors, 1,7-perylene-3,4,9,10-tetracarboxylic tetrabutylester (A1), 1,7-perylene-3,4,9,10-tetracarboxylic monoimide dibutylester (A2), and 1,7-perylene-3,4,9,10-tetracarboxylic bisimide (A3). The energy donors have been linked at the 1,7-bay-positions of the perylene derivatives, thus leaving the peri positions free for further functionalization and device construction. A highly stable and rigid structure, with no electronic communication between the donor and acceptor components, has been realized via an all-aromatic non-conjugated phenoxy spacer between the constituent chromophores. The selection of donor naphthalene derivatives for attachment with perylene derivatives was based on the effective matching of their respective optical properties to achieve efficient excitation energy transfer (EET) by the Förster mechanism. A comprehensive study of the excited-state dynamics, in toluene, revealed quantitative and ultrafast (ca. 1 ps) intramolecular EET from donor naphthalene chromophores to the acceptor perylenes in all the studied systems. Electron transfer from the donor naphthalene chromophores to the acceptor perylenes has not been observed, not even for antenna systems in which this process is thermodynamically allowed. Due to the combination of an efficient and fast energy transfer along with broad absorption in the visible region, these antenna systems are promising materials for solar-to-electric and solar-to-fuel devices.

Graphical abstract: Tunable and highly efficient light-harvesting antenna systems based on 1,7-perylene-3,4,9,10-tetracarboxylic acid derivatives

Supplementary files

Article information

Article type
Edge Article
Submitted
26 jan. 2016
Accepted
08 mar. 2016
First published
15 mar. 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 3517-3532

Tunable and highly efficient light-harvesting antenna systems based on 1,7-perylene-3,4,9,10-tetracarboxylic acid derivatives

R. K. Dubey, D. Inan, S. Sengupta, E. J. R. Sudhölter, F. C. Grozema and W. F. Jager, Chem. Sci., 2016, 7, 3517 DOI: 10.1039/C6SC00386A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, 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 commercial 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