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Donor‐Acceptor‐Donor Thienopyrazine‐Based Dyes as NIR‐Emitting AIEgens
Author(s) -
Goti Giulio,
Calamante Massimo,
Coppola Carmen,
Dessì Alessio,
Franchi Daniele,
Mordini Alessandro,
Sinicropi Adalgisa,
Zani Lorenzo,
Reginato Gianna
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100199
Subject(s) - tetraphenylethylene , chemistry , moiety , photochemistry , acceptor , aggregation induced emission , pyrazine , luminescence , absorption (acoustics) , stokes shift , combinatorial chemistry , optoelectronics , stereochemistry , fluorescence , materials science , physics , quantum mechanics , composite material , condensed matter physics
Organic Near‐Infrared luminophores have found broad application as functional materials, but the development of efficient NIR emitters is still a challenging goal. Here we report on a new class of thieno[3,4‐ b ]pyrazine‐based NIR emitting materials with Aggregation Induced Emission (AIE) properties. The dyes feature a donor–acceptor–donor (D−A−D) structure, with a thienopyrazine acceptor core connected to two triarylamine donor groups bearing a tetraphenylethylene (TPE) moiety. Fast and efficient synthesis allowed the modular preparation of three dyes of tunable absorption and emission profiles. These constructs were extensively characterized by spectroscopic studies in different solvents, which revealed intense light‐harvesting ability and emissions in the deep‐red and NIR region with large Stokes shift values. Remarkably, the dyes exhibited AIE properties, retaining emissive ability in the aggregate state, thus emerging as attractive materials for their potential application in the development of luminescent devices.