Synthesis, Photophysical and Electrochemical Properties of Bis‐Squaraine Dyes Fused on Isomeric Benzodipyrrole Central Units

Sawada, Ryuhei ; Maeda, Takeshi ; Oda, Yuya ; Yagi, Shigeyuki ; Karunakaran, Venugopal ; Fujiwara, Hideki ; Ajayaghosh, Ayyappanpillai (2022) Synthesis, Photophysical and Electrochemical Properties of Bis‐Squaraine Dyes Fused on Isomeric Benzodipyrrole Central Units Chemistry – An Asian Journal, 17 (13). ISSN 1861-4728

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Official URL: http://doi.org/10.1002/asia.202200227

Related URL: http://dx.doi.org/10.1002/asia.202200227

Abstract

Exciton interactions are not only observed in assembled molecules but also in compounds with multiple chromophores referred to as superchromophores. We have developed isomeric bis-squaraine dyes as superchromophores in which two squaraine chromophores are fused onto the isomeric benzodipyrrole skeleton so as to regulate conformations and to reduce distances between two chromophores. The dyes with benzo[1,2-b:3,4-b’]dipyrrole and benzo[1,2-b:5,4-b’]dipyrrole moieties exhibited split electronic absorption originated from the intramolecular exciton interaction. The intensity of the split absorption bands varies in correlation with the orientation of chromophores. The isomeric dye with benzo[1,2-b:4,5-b’]dipyrrole moiety exhibited a near-infrared absorption associated with the resonance throughout two chromophores. Their electrochemical and spectroelectrochemical properties are distinct from those of monomeric dyes owing to electronic interactions between the two chromophores. Thus, the structural isomerism of the central skeleton significantly affects their optical properties as well as their electrochemical properties.

Item Type:Article
Source:Copyright of this article belongs to John Wiley & Sons, Inc.
ID Code:129866
Deposited On:25 Nov 2022 10:46
Last Modified:25 Nov 2022 10:46

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