9-Arylvinyl- and 9,10-bis(arylvinyl)-anthracenes with phenyl and naphthyl as aryl moieties: Differential aggregation behaviors and optoelectronic properties

Abstract

In this paper, we have synthesized four simple twisting arylvinyl anthracene derivatives, 9-styrylanthracene (ASB), 9,10-bis(styryl)anthracene (SB), 9-(2-(naphthalen-1-yl)vinyl)anthracene (ASN) and 9,10-bis((naphthalen-1-yl)vinyl)anthracene (SN), to demonstrate the effect of skeleton symmetry on optical and optoelectronic properties. The results showed that SB and SN are weak emission with the fluorescence quantum yields (Φ) of ca. 7 % but ASB and ASN are highly fluorescent (Φ ≈ 50 %) in THF solution, although they all exhibit high solid-state fluorescence efficiencies (22 ~ 50 %). Grinding could induce about 20 nm of spectral shift of ASB and ASN crystalline fluorescence, but SB and SN crystals hardly exhibit mechanofluorochromic behavior. Furthermore, the evaporated films of SB and SN are fragile due to re-crystallization soon, but those of ASB and ASN are stable and could be used as the bulk emissive layer exhibiting commendable electroluminescent performances. This finding indicates that the geometric structures of conjugated skeletons could influence the electronic and aggregate structure of organic luminogens, and then alter their optical and optoelectronic properties.

Magneto-conductance characteristics of trapped triplet–polaron and triplet–trapped polaron interactions in anthracene-based organic light emitting diodes

“…Moreover, anthracene and its derivatives are widely used as the active layer in organic devices, and so their physicochemical properties and the spin dependent processes that occur within these devices are well documented. 19,[42][43][44][45][46][47][48] In this paper, we describe the investigation of the MC characteristics of T t PI and TP t I in anthracene-based OLEDs. The EL spectra, MEL curves and current-voltage characteristics indicated that the active anthracene layer contained large amounts of trapped singlet excitons (S 1t ), T t and P t .…”

Supramolecular Interactions‐Assisted Polymorphism and Unique Mechanofluorochromism in 9,10‐Bis((E)‐4‐(trifluoromethyl)styryl)anthracene

“…The conformationally controlled intramolecular torsional motions between the anthrylene center and vinylene fragments linked at 9, 10 positions play a great role in the observed AIEE phenomenon [2] . Also, the twisted molecular architecture originates from the strong repulsion between the 1, 4, 5, 8 positions in the anthracene moiety, and the aryl/vinyl substituent attached at 9, 10 positions facilitates the torsional motions in DSA derivatives [3] . A large number of AIEE active DSA derivatives were systematically investigated for the diverse applications till now.…”

“…[2] Also, the twisted molecular architecture originates from the strong repulsion between the 1, 4, 5, 8 positions in the anthracene moiety, and the aryl/vinyl substituent attached at 9, 10 positions facilitates the torsional motions in DSA derivatives. [3] A large number of AIEE active DSA derivatives were systematically investigated for the diverse applications till now. Recently multi aryl cyano substituted DSA derivatives were effectively utilized for the rewritable paper technology applications.…”

“…(3,4,5,6) is 74.58 ο and in 4FDSA-O, θ(3,4,5,6) is 53.01 ο . This decrease in the torsional angle in 4FDSA-O leads to more planarization of the molecule and thus an increase in effective conjugation, which in turn leads to red shifted…”

Aggregation‐induced emission enhancement of anthracene‐derived Schiff base compounds and their application as a sensor for bovine serum albumin and optical cell imaging

“…Attaching Schiff base derivatives to organic or metal units to serve as optical sensors is a good approach for study . Only a few reports on anthracene derivatives are available, and these show high fluorescence efficiency in their solid states and the AIE/AIEE phenomenon . In addition, efforts have been made to design organic fluorophores coupled with the dynamic interactions of biologically important species that can be visualized by fluorescence microscopy .…”