Synthesis and luminescence properties of functionalized V-shaped bis-coumarin derivatives

Abstract

Three new functionalized V-shaped bis-coumarin derivatives, 3-(diethylamino)-10-(4-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-6H,7H-chromeno[3,4-c]chromene-6,7-dione (VBC-BI), 3-(diethylamino)-10-(10H-phenothiazin-10-yl)-6H,7H-chromeno[3,4-c]chromene-6,7-dione (VBC-PTZ) and 3-(diethylamino)-10-(9H-carbazol-9-yl)-6H,7H-chromeno[3,4-c]chromene-6,7-dione (VBC-Cz), were successfully synthesized and characterized. Among them, the structures of VBC-PTZ and VBC-Cz were characterized by single...

AIEE-active V-shaped fused-biscoumarins: synthesis, photophysical and electroluminescence properties

“…1A, there are two molecules in the crystal structure of CC-TriPE , each V-shaped fused-biscoumarin core in both CC-TriPE molecules is not in a plane, and the twist angles between two single coumarin rings are 23.38° and 26.23°, respectively. These twist angles are much larger than that of the previously reported V-shaped fused-biscoumarin derivatives (4.00–8.00°), 36,37 which could be a result of the steric hindrance of the triphenylethene group. Furthermore, in the crystal lattice of CC-TriPE , there are four CC-TriPE molecules, and there are strong π–π stacking interactions through the fused biscoumarin skeletons (3.432 Å) between the two adjacent molecules (Fig.…”

“…The intense absorption bands at 297 nm for CC-TPE and 295 nm for CC-TriPE could be assigned to the pp* transitions of the tetraphenylethylene and triphenylethylene moieties, 21,[40][41][42] and the moderate absorption bands at 391 nm for CC-TPE and 402 nm for CC-TriPE could be ascribed to the pp* transitions of the V-shaped fused-biscoumarin skeletons. 36,37 The strong absorption band at 464 nm of CC-TPE and CC-TriPE could be attributed to the intramolecular charge transfer (ICT) transitions from the tetraphenylethylene and triphenylethylene moieties to the V-shaped fused-biscoumarin cores, 35 respectively. The compound CC-TPA exhibited two intense absorption bands at 300 and 455 nm, and the former band could be attributed to the pp* transitions of the triphenylamine moiety, while the latter could be assigned to the ICT transition from the triphenylamine moiety to the V-shaped fused-biscoumarin core.…”

“…In view of the structure and promising photoelectronic properties of the V-shaped fused-biscoumarin and our previous studies, 36,37 in this paper, three new AIEE-active Vshaped fused-biscoumarin derivatives, CC-TPA, CC-TPE and CC-TriPE, were successfully designed and synthesized by introducing triphenylamine (TPA), tetraphenylethene (TPE) and triphenylethene (TriPE) groups into the V-shaped fusedbiscoumarin core for application in organic-light emitting devices. The electrochemical and photophysical properties, thermal stabilities and electroluminescence performances of the compounds were investigated systematically.…”