Bis(tetrathiafulvaleno)octadehydro[20]annulene with Multi-functionality

Abstract

Sulfur-bridged octadehydro[20]annulene 1c annelated with two TTF rings was synthesized and its multi-functional properties were ascertained. The annulene exhibits paratropicity, solvatochromism, electrochromism and multi-redox potentials in solution, and its cation radical in the solid state shows self-association and electric conductivity.

Bi-TTF, Bis-TTF, and Related TTF Oligomers

“…The TTF-annelated [12]annulenes 101 and 102 exhibit π-amphoteric properties based on the TTF donor and [12]annulene acceptor. 68,69 A polymeric TTF derivative 103 and a poly(TTFthiophene) system 104 have been reported by Yamamoto and Shimizu. 70 Extended π-conjugation in polymers 103 and 104 is evident from a red shift in their electronic spectra.…”

“…Conjugated bis-TTFs linked to macrocycles and polymers (Chart ) have been investigated for the construction of multifunctional π-systems and conducting polymers. The TTF-annelated [12]annulenes 101 and 102 exhibit π-amphoteric properties based on the TTF donor and [12]annulene acceptor. , A polymeric TTF derivative 103 and a poly(TTF-thiophene) system 104 have been reported by Yamamoto and Shimizu . Extended π-conjugation in polymers 103 and 104 is evident from a red shift in their electronic spectra.…”

Size-Selective Recognition by a Tubular Assembly of Phenylene–Pyrimidinylene Alternated Macrocycle through Hydrogen-Bonding Interactions

“…From a fundamental point of view, shape-persistent and fully π-conjugated macrocycles possess structural superiority, because they not only supply an intrinsic inner cavity for the guest molecules but also form 1D tubular objects through an intermolecular π–π interaction. Consequently, a variety of fully π-conjugated macrocyclic derivatives with different skeletons and cavities have been developed as efficient artificial building blocks. − So far, by precision molecular design, fully π-conjugated macrocycles composed of porphine, − pyridine, − thiophene, , carbazole, ,,,, and other moieties with various internal cavities have been synthesized to respond to an external stimulus by means of well-known host–guest chemistry. − Most of these macrocycles show excellent self-assembly properties in solution forming various nano-objects, such as nanowires, − spherical structures, − tubular objects, − as well as two-dimensional (2D) sheets. Therein, nanotubes possessing structural fascination with a uniform inner diameter and large 1D hollow channels are used in many applications, including use as transporting materials, encapsulation of guest molecules, and soft templates.…”

A rational strategy for improving air-stability of OFETs via electronic tuning of substituents of benzene-fused bis(tetrathiafulvalene)

“…Compound 4 and 5a were synthesized according to the literature procedure. 12,13 The synthesis procedures and characterization of compounds 5bed are provided in the Supplementary data. and toluene (10 mL) were added in 100 mL reaction bulb, the mixture was refluxed for 10 min under a nitrogen atmosphere at 120 C. When the compound 4 was dissolved, compound 5(2.4 g, 6.19 mmol) and P(OEt) 3 (7 mL) were slowly dropped to the mixture, then refluxed for 30 min.…”