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Room Temperature Phosphorescence from Organic Materials: Unravelling the Emissive Behaviour of Chloro‐Substituted Derivatives of Cyclic Triimidazole
Author(s) -
Giannini Clelia,
Forni Alessandra,
Malpicci Daniele,
Lucenti Elena,
Marinotto Daniele,
Previtali Andrea,
Carlucci Lucia,
Cariati Elena
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.202100131
Subject(s) - phosphorescence , chemistry , bromine , time dependent density functional theory , fluorescence , aggregation induced emission , photochemistry , triazine , combinatorial chemistry , organic chemistry , molecule , physics , quantum mechanics
Purely organic luminophores that exhibit room temperature phosphorescence (RTP) are receiving an ever‐growing attention. The design of efficient RTP materials and the understanding of their emissive behaviour, however, remain a challenging task. Herein, to gain further insights into metal‐free RTP, we report the synthesis, characterization, and photophysical study of chloro‐derivatives of [1,2‐ a :1′,2′‐ c :1′′,2′′‐ e ][1,3,5]triazine or cyclic triimidazole ( TT ). Mono‐ ( 1Cl ), di‐ ( 2Cl ) and tri‐chloro‐ TT ( 3Cl ) derivatives are prepared by mild chlorination with N ‐chlorosuccinimide (NCS). The three compounds are characterized by aggregation‐induced emission (AIE) comprising dual fluorescence and multiple phosphorescences, whose origin is disclosed by crystal structure analysis together with accurate DFT/TDDFT calculations. Comparison with previously reported bromine and iodine TT derivatives reveals the new chlorinated compounds as the best performing halogenated AIE members of the family.