CH⋅⋅⋅π Interaction‐Modulated Solid‐State Packing and Carrier Mobility in Thienyl and Thieno[3,2‐b]Thienyl End‐Capped Distyrylarylene Derivatives

Abstract

Research on structure-property relationships in distyrylarylene derivatives is far behind their wide applications in optoelectronic devices due to the absence of crystal structure information. Herein, the single crystals of 4,4'-bis(2-thienylvinyl)biphenyl (1) and 4,4'-bis(2-thieno[3,2-b]thienylvinyl)biphenyl (2) were successfully grown by the vapor transport method. Both molecules adopt the typical herringbone packing motif. However, the intermolecular C-H⋅⋅⋅π interaction in compound 2 is much stronger than that in compound 1. The correlations of interchain interaction with film morphology, optical and electronic properties were studied. Compound 2 formed higher crystalline films with (001) and (111) orientations. The organic field-effect transistor properties of both materials were investigated. Compound 2 showed better performance with a hole mobility higher than 0.01 cm(2) V(-1) s(-1) and an on/off current ratio over 10(6) . These results reveal that the intensity of C-H⋅⋅⋅π interactions can exert dramatic influences on the optical and electronic properties of distyrylarylene-based materials.

Molecular engineering of excited-state process for multicolor microcrystalline lasers

“…1a), including 4,4 0 -bis(2-thienyl-vinyl)biphenyl (BPVT), 4,4 0 -bis(2-bithienylvinyl)biphenyl (BBTVB), and 4,4 0 -bis(2-terthienyl-vinyl)biphenyl (BTTVB), were synthesized through the Horner-Wadsworth-Emmons reaction. 20 The details on the synthesis, purification, and characterization of the chemical properties of three compounds are provided in ESI † (Scheme S1 and Fig. S1, S2).…”

“…It can be identified that the monoclinic BPVT crystal belongs to the space group of P2 1 (CCDC no. 796660) 20 with cell parameters of a = 6.073 Å, b = 7.496 Å, c = 19.872 Å, and a = b = g = 901 (Table S2, ESI †). Based on the abovementioned cell parameters, the red circle and green triangle sets of spots in the SAED pattern of BPVT EHMSs (Fig.…”

“…The distyryl-framework derivative is one kind of excellent emitting material that is widely used in efficient electroluminescence (EL) devices. [19][20][21][22][23][24][25][26] For instance, Tao et al reported on the characteristics of thin-film transistors made up of distyryl thiophene-substituted molecules. 19,20 Adachi et al reported on the quasi-continuous-wave and current-injection OSSLs based on the blend thin films consisting of distyryl-framework molecules and host material.…”

“…[19][20][21][22][23][24][25][26] For instance, Tao et al reported on the characteristics of thin-film transistors made up of distyryl thiophene-substituted molecules. 19,20 Adachi et al reported on the quasi-continuous-wave and current-injection OSSLs based on the blend thin films consisting of distyryl-framework molecules and host material. 11,27 However, abundant grain boundaries and defects in organic thin films make them unsuitable to gain an insight into the intrinsic properties of organic photoelectric devices.…”