Rigid Annulated Carbon–Sulfur Structures

Torroba, Tomás; Garcı́a-Valverde, Marı́a

doi:10.1002/anie.200603461

Cited by 32 publications

(11 citation statements)

References 65 publications

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“…Different from the commonly studied thiophene oligomers20, 1 has an elegant molecular structure of a cycle of eight annulated thiophenic rings and contains no hydrogen atom (Fig. 1).…”

mentioning

confidence: 98%

Impact of heterocirculene molecular symmetry upon two-dimensional crystallization

Xiao

Zhang

Lei

et al. 2014

Sci Rep

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Despite the development of crystal engineering, it remains a great challenge to predict the crystal structure even for the simplest molecules, and a clear link between molecular and crystal symmetry is missing in general. Here we demonstrate that the two-dimensional (2D) crystallization of heterocirculenes on a Au(111) surface is greatly affected by the molecular symmetry. By means of ultrahigh vacuum scanning tunneling microscopy, we observe a variety of 2D crystalline structures in the coverage range from submonolayer to monolayer for D8h-symmetric sulflower (C16S8), whereas D4h-symmetric selenosulflower (C16S4Se4) forms square and rectangular lattices at submonolayer and monolayer coverages, respectively. No long-range ordered structure is observed for C1h-symmetric selenosulflower (C16S5Se3) self-assembling at submonolayer coverage. Such different self-assembly behaviors for the heterocirculenes with reduced molecular symmetries derive from the tendency toward close packing and the molecular symmetry retention in 2D crystallization due to van der Waals interactions.

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“…Different from the commonly studied thiophene oligomers20, 1 has an elegant molecular structure of a cycle of eight annulated thiophenic rings and contains no hydrogen atom (Fig. 1).…”

mentioning

confidence: 98%

Impact of heterocirculene molecular symmetry upon two-dimensional crystallization

Xiao

Zhang

Lei

et al. 2014

Sci Rep

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“…Self‐assembly has extensively been used for constructing the regular shaped molecules . Over the last decades, shape‐persistent conjugated cyclic molecules composed of benzene, thiophene, pyridine, and acetylene moieties have been prepared . In particular, Si‐containing π‐conjugated macrocycles possessing the interesting properties, including excellent heat, radiation, chemical resistance, film‐forming ability and low dielectric constants.…”

Section: Figurementioning

confidence: 99%

Synthesis and Cyclization‐Induced Charge Transfer of Rectangular Bisterthiophenesiloxanes

Tashiro

et al. 2019

Chemistry A European J

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Cyclization‐modified terthiophene displays the change of emission behavior from locally excited (LE) to the intramolecular charge transfer (ICT) state. The rectangular bisterthiophenesiloxanes (DSiTh) was successfully prepared by π–π‐stacking‐aided hydrogen‐bonding interactions. Cyclization‐induced ICT in DSiTh could be observed, which was confirmed by absorption spectra, fluorescence spectra, and quantum chemistry analysis. The cyclization produces a strong intramolecular electron redistribution of a highly packed π‐conjugated terthiophene. Thus, a distinctive variation of the dipole moment and a through‐space ICT happen.

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“…There is an ever growing interest in carbon-sulfur compounds due to their potential applications in organic electric devices such as organic field-effect transistors (OFETs), light-emitting diodes, photovoltaic cells and light modulators [1][2][3]. Octathio [8]circulene (1), called 'sulflower' (see Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Octathio [8]circulene (1), called 'sulflower' (see Fig. 1), is a newcomer in this materials family [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Electrochemical field-effect transistors of octathio[8]circulene robust thin films with ionic liquids

Fujimoto

Matsushita

Awaga

2009

Chemical Physics Letters

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Rigid Annulated Carbon–Sulfur Structures

Cited by 32 publications

References 65 publications

Impact of heterocirculene molecular symmetry upon two-dimensional crystallization

Impact of heterocirculene molecular symmetry upon two-dimensional crystallization

Synthesis and Cyclization‐Induced Charge Transfer of Rectangular Bisterthiophenesiloxanes

Electrochemical field-effect transistors of octathio[8]circulene robust thin films with ionic liquids

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