Novel green-yellow-orange-red light emitting donor-π-acceptor type dyes based on 1,3-indandione and dimedone moieties

Synthesis, Structures, and Photophysical Properties of Alternating Donor–Acceptor Cycloparaphenylenes

“…[6] The maximum absolute fluorescence quantum yields (F F )o f1a and 2a were 0.59 and 0.23, respectively,w hich are higher than that of 3a (F F = 0.044) [9a] but lower than that of [12]CPP (F F = 0.89). [6] As expected, solvatofluorochromism [16] was observedi n1a and 2a.S olutionso f1a were observed to undergo modest changes in fluorescencec olor,f rom deep blue in hexane-CHCl 3 to green in CH 3 CN-CHCl 3 .M ore significant solvatofluorochromism was observedi ns olutions of 2a from deep blue in hexane-CHCl 3 to yellow in CHCl 3 ,a lthough fluorescence quenching was observed in CH 3 CN-CHCl 3 .…”

“…[8] This compound also showed as mall HOMO-LUMO gap. [9] In this paper,w ed isclose the synthesis of alternating donor-acceptor [12]CPPs 1a-c and 2a (Figure 1), and [16]CPP by macrocyclization by the rhodium-catalyzed intermolecularc ross-cyclotrimerization of ad iyne, possessing a1 ,4-dimethoxy-5,8-dihydronaphthalene unit, with acetylenedicarboxylates followed by imidation and/oraromatization. Recently,o urs and other groups have synthesized severals ymmetrically multi-functionalized CPPs, [9][10][11] such as [12]CPP-hexacarboxylate 3a ( Figure 1).…”

“…Scheme1 shows the synthesis of the alternating donor-acceptor [12] and [16]CPPs.T he Sonogashira coupling of known dibromide 4 [10a] with trimethylsilylacetylene followed by desilylation afforded diyne 5.T he intermolecularc ross-cyclotrimerization of 5 and di-tert-butyl acetylenedicarboxylate (6a)i nt he presenceo faRh I + /H 8 -binap [2,2'-bis(diphenylphospino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl] catalyst [12] proceeded to give [12]CPP precursor 7a.S urprisingly,h ighly strained [16]CPP precursor 8a was also generated. Subsequento xidative aromatization of 7a and 8a with DDQ [10] gave alternating donor-acceptor [12]CPP 1a and [16]CPP 10 a.N ot only di-tertbutyl (6a)b ut also diethyl( 6b)a nd dimethyl (6c)a cetylenedicarboxylates could be employed for this process to give [12]CPPs 1b,c,w hile [16]CPPs 10 b,c could not be isolated cleanly.I nterestingly,h ighly strained [ 8]CPP precursors 9b,c were also isolated, although their aromatization with DDQ did not afford [8]CPPs.T he intermolecular cross-cyclotrimerization of 5 and 6c followed by imidation [10d] with tert-butylamine and oxidative aromatization afforded [12]CPP 2a,p ossessing an imide acceptor unit.…”

“…In summary,w eh ave achieved the synthesis of alternating donor-acceptor [12] and [16]CPPs by the rhodium-catalyzed intermolecular cross-cyclotrimerization of ad iyne,p ossessing a1 ,4-dimethoxy-5,8-dihydronaphthalene unit, with acetylenedicarboxylates followed by imidation and/or aromatization. It was found that thus obtained [12]CPP 1a forms the columnar packing through CH-p and p-p stacking interactions in the crystals, despite the presence of three bulky phthalate and dimethoxynaphthaleneu nits.…”

Tuning Emitting Color of Electroluminescent Devices Containing Tris(2‑acyl‑1,3‑indandionate)aluminum(III) Complexes as Emitting Layers

“…32 Furthermore, recent studies have investigated the effect of p-linker length connecting donor and acceptor groups on several properties of cyclic β-diketones-1,3-indandiones, such as thermal, electrochemical, and spectroscopic properties. 33 Experimental results have also revealed that frontier orbitals for 2-acyl-1,3-indandione (acind) ligands presenting methyl and phenyl donor groups are generally located at low energies. However, acind ligands containing aromatic substituent groups generally present HOMO at lower energies than those ones with aliphatic groups.…”