Unequal Perylene Diimide Twins in a Quadruple Assembly

Author:

Chen Shuqi1,Feng Shishi2,Markvoort Albert J.3,Zhang Cankun4,Zhou Enyang5,Liang WanZhen2,Zhang Hui‐Jun1,Jiang Yun‐Bao1,Lin Jianbin1ORCID

Affiliation:

1. Department of Chemistry College of Chemistry and Chemical Engineering MOE Key Laboratory of Spectrochemical Analysis and Instrumentation Xiamen University Xiamen 361005 P. R. China

2. State Key Laboratory of Physical Chemistry of Solid Surfaces iChEM Department of Chemistry College of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China

3. Computational Biology Group and Institute for Complex Molecular Systems Eindhoven University of Technology PO Box 513 5600 MB Eindhoven (The Netherlands

4. Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM) Xiamen 361005 P. R. China

5. School of Mathematical Sciences Xiamen University Xiamen 361005 P. R. China

Abstract

AbstractNatural light‐harvesting (LH) systems can divide identical dyes into unequal aggregate states, thereby achieving intelligent “allocation of labor”. From a synthetic point of view, the construction of such kinds of unequal and integrated systems without the help of proteinaceous scaffolding is challenging. Here, we show that four octatetrayne‐bridged ortho‐perylene diimide (PDI) dyads (POPs) self‐assemble into a quadruple assembly (POP)4 both in solution and in the solid state. The two identical PDI units in each POP are compartmentalized into weakly coupled PDIs (P520) and closely stacked PDIs (P550) in (POP)4. The two extreme pools of PDI chromophores were unambiguously confirmed by single‐crystal X‐ray crystallography and NMR spectroscopy. To interpret the formation of the discrete quadruple assembly, we also developed a two‐step cooperative model. Quantum‐chemical calculations indicate the existence of multiple couplings within and across P520 and P550, which can satisfactorily describe the photophysical properties of the unequal quadruple assembly. This finding is expected to help advance the rational design of dye stacks to emulate functions of natural LH systems.

Funder

National Natural Science Foundation of China

Publisher

Wiley

Subject

General Medicine

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