Quest for a Rational Molecular Design of Alkyl‐Distyrylbenzene Liquid by Substitution Pattern Modulation. Issue 21 (13th March 2023)

• Record Type: Journal Article
• Authors: Zheng, Xiao; Nagura, Kazuhiko; Takaya, Tomohisa; Hashi, Kenjiro; Nakanishi, Takashi
• Is Part Of: Chemistry. Volume 29:Issue 21(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-03-13
• Subjects: #alkyl-π functional molecular liquids -- distyrylbenzene -- luminescence -- substitution pattern modulation -- viscosity; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202203775
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Alkyl‐π functional molecular liquids (FMLs) are of interest for fabricating soft electronic devices due to their fluidic nature and innate optoelectronic functions from the π‐conjugated moiety. However, predictable development of alkyl‐π FMLs with the desired liquid and optoelectronic properties is challenging. A series of alkyl‐distyrylbenzene (DSB) liquids was studied in terms of the substituent position effect by attaching 2‐octyldodecyl chains at (2, 4‐), (2, 5‐), (2, 6‐), and (3, 5‐). The effect of the alkyl chain length was investigated by attaching 2‐hexyldecyl, 2‐decyltetradecyl (C10 C14 ), and 2‐dodecylhexadecyl at the (2, 5‐) substituent position. The 2, 5‐C10 C14 substituent pattern constructed a superior alkyl‐DSB liquid with a lower viscosity, intrinsic optical properties, and high thermal‐ and photo‐stabilities. The discovered 2, 5‐C10 C14 was applied to dicyanostyrylbenzene and comparable liquid physical and optical superiorities were confirmed. This molecular design is useful for creating alkyl‐π FMLs with the aforementioned advantages, which are applicable for deformable and flowable optoelectronic devices. Abstract : Via modulation of the substitution pattern, 2‐decyltetradecyl chains at the 2, 5‐substituted position was found to be the desired substitution pattern for alkyl‐distyrylbenzene liquids exhibiting the lowest viscosity as a practically stable liquid at room temperature, intrinsic optical properties, as well as high thermal‐ and photo‐stabilities. The guiding strategy will be useful for constructing superior alkyl‐π FMLs with rich optoelectronic properties.