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

In this paper, we have synthesized our simple twisting arylvinyl anthracene derivatives, 9-styrylanthracene (ASB), 9,10-bis(styryl)anthracene (SB), 9-(2-(naph- thalen-l-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 (Phi) of ca. 7% but ASB and ASN are highly fluorescent (Phi approximate to 50%) in THE solution, although they all exhibit high solid-state fluorescence efficiencies (22 similar to 50%). Grinding could induce about 20 nm of spectral shift of ASB and ASN crystalline fluorescence, but SB and SN crystals hardly exhibit mechano- fluorochromic 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. (C) 2016 Elsevier B.V. All rights reserved.