Absolute configuration and chiral self-assembly of rubrene on Bi(111)

Abstract

We investigated the chiral self-assembly of rubrene molecules on a semi-metallic Bi(111) surface using low-temperature scanning tunneling microscopy. The absolute configuration of isolated rubrene enantiomers was identified from high-resolution images. Two types of homochiral domains of rubrene monomers and hexamers were observed, respectively. For rubrene monomers, chiral separation was spontaneous with each chiral monomer appearing in their respective domain. For rubrene hexamers, two levels of organization chirality were recorded: one is six heterochiral rubrene molecules arranged alternatively in a rubrene hexamer; and the other is a homochiral arrangement of individual hexamers. After annealing at 350 K, a large area of supramolecular self-assembled L- and R-type triangular heterochiral hexamers was obtained at the narrow terrace of Bi(111). Moreover, a molecular chiral inversion from the L-(R-) type to the R-(L-) type occurs during the formation of the hexamer domain structure and can be attributed to the enhanced intermolecular interactions governed by the intensive intermolecular extrusion at the narrow terrace.

Scanning tunneling microscopy and spectroscopy of rubrene on clean and graphene-covered metal surfaces

“…Inside the row, pairs of β-molecules orient the upward tilted part of their tetracene backbone towards each other. The coexistence of different C 42 H 28 configurations was previously reported for a variety of surfaces [25,35,36] and is not specific to graphene.…”

“…In that work a multilayer C 42 H 28 film was deposited at room temperature and subsequently annealed to achieve a monolayer coverage. Different superstructures of C 42 H 28 with twisted and tilted backbones were presented in [ 25 – 27 34 ] for Au(111) and in [ 35 ] for Bi(111). In these reports, the deposition of molecules was performed at 5 K [ 25 – 27 34 ] and 100 K [ 35 ] with subsequent annealing at room temperature [ 25 – 27 34 ] and 350 K [ 35 ].…”

“…Different superstructures of C 42 H 28 with twisted and tilted backbones were presented in [ 25 – 27 34 ] for Au(111) and in [ 35 ] for Bi(111). In these reports, the deposition of molecules was performed at 5 K [ 25 – 27 34 ] and 100 K [ 35 ] with subsequent annealing at room temperature [ 25 – 27 34 ] and 350 K [ 35 ]. Therefore, deposition at low temperature seems to favor the adsorption with twisted and tilted backbones, possibly due to an initial high density of small island with chiral molecules, while the subsequent annealing preserves the twisted and tilted configuration of the molecular backbone and leads to homochiral domains.…”

Structure transition of a C60 monolayer on the Bi(111) surface

“…31 However, few reports address the superstructure of C 60 molecules adsorbed on semi-metal substrates. It is found that thin lms of organic molecules grown on a semi-metallic Bi(111) surface shows a lot of interesting phenomena, such as the ordered crystalline layer with the standing-up orientation of pentacene molecules, 32 the chiral self-assembly of rubrene molecules, 33 structural transitions in different monolayers of cobalt phthalocyanine lms, 34 and the Moire' pattern in C 60 thin lms. 35 In this study, we use Bi(111) as the substrate and studied the structure transition of the C 60 monolayer.…”

A new phase of rubrene monoclinic crystals on Cd(0001)

“…2010年, Huang等 人 [29] 用化学反应法得到红荧烯晶体, 采用单晶X射线 衍射证明两种晶体分别是单斜晶体和三斜晶体. 在 2014年, Obata等人 [33] [1,16] . 因此, 在 中可以看到并四苯几乎垂直于基底 [34,35] .…”