Abstract
A series of perylenetetracarboxylic diimides (PDIs) dimers with slipped “face-to-face” stacked structure and different substituents at the bay positions have been synthesized and the molecular structures are characterized by 1H NMR, MALDI-TOF and elemental analysis. And different substituents at the bay positions of the PDI ring bring about various steric hindrances. These different steric hindrances have caused significant differences on the absorption and emission spectra. The correlation between the photophysical properties and the molecular structure is discussed.
Highlights
In natural light-harvesting systems, a slipped arrangement of chlorophyll dyes is accomplished by proteins or metal-ion coordination, providing J-type aggregates [1]
The difference on the number or species of side groups attached at the bay positions of the perylenetetracarboxylic diimides (PDIs) rings in these dimers induces different degrees of slipping and/or rotation of the two PDI rings relative to each other, which can lead to different electronic coupling between the two PDI subunits in these compounds
It has been proved that introducing different substituents at the bay positions of the PDI ring is an efficient way to change photophysical properties of PDI compounds [17]
Summary
In natural light-harvesting systems, a slipped arrangement of chlorophyll dyes is accomplished by proteins or metal-ion coordination, providing J-type aggregates [1]. Many chromophores were constructed into J-aggregates by self-assemble process Among these dyes, porphyrin dyes [2] are the most popularly investigated organic dyes because of their similar molecular structure and photophysical properties with natural bacteriochlorophyll a (Bchl a) molecules [3] [4]. A series of covalently linked core-substituted PDI dimers and trimers with diphenoxyl groups have been reported by our group [10]. In both of these studies, the degree of slipping of the two PDI chromophores is tuned by changing the spacer, which can affect the photophysical property of J-aggregate. The difference on the number or species of side groups attached at the bay positions of the PDI rings in these dimers induces different degrees of slipping and/or rotation of the two PDI rings relative to each other, which can lead to different electronic coupling between the two PDI subunits in these compounds
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