Preparation and physicochemical studies of new multiple rings s-tetrazines

Abstract

Several new supramolecular s-tetrazines have been prepared and studied. Their electrochemical and spectroscopic properties have been investigated, especially in the presence of quenchers. Fluorescence quenching has been shown to occur as expected through a charge transfer mechanism and the cyclophane structure has been shown to lead to an acceleration of the quenching process.Scheme 1 Formula of the s-tetrazines.

Electronic Structure and Charge Transport Properties of a Series of 3,6-(Diphenyl)-s-tetrazine Derivatives: Are They Suitable Candidates for Molecular Electronics?

“…The synthesis of bis(3,5-difluorophenyl)-s-tetrazine, (F 2 Ph) 2 Tz, was performed via a Pinner-type reaction between 3,5-difluorobenzonitrile and hydrazine, 8,27 with N-acetylcysteine as catalyst (Scheme S1). Hydrazine hydrate (2.9 mL, 58.46 mmol) was dropwise added to a solution of 3,5-difluorobenzonitrile (2 mL, 58.46 mmol) and N-acetylcysteine (3.3 g, 19.49 mmol) in MeOH (20 mL) at room temperature, and the resulting mixture was stirred for 24 h at reflux temperature under Ar atmosphere.…”

“…redox reversibility on reduction and exhibit low potentials 2,4,5 and also they are coloured due to a n → π* low energy transition. [5][6][7][8] In addition, several tetrazine derivatives are fluorescent in the visible wavelength region, λ max ~ 550-570 nm).…”

“…Tetrazine derivatives constitute the most electron-deficient aromatic family [1][2][3] and display interesting properties as concern semiconducting and opto-electronic applications, e.g. redox reversibility on reduction and exhibit low potentials 2,4,5 and also they are coloured due to a n → π* low energy transition.…”

“…Perfluoropentacene constitutes a nice example as it exhibits electron mobility (µ) values as high as 0.22 cm 2 V -1 methods. The electron transport properties were evaluated on molecular crystals modeled from the X-ray crystal structure of (F 2 Ph) 2 Tz. Chart 1.…”

“…70 All the atomic positions and lattice parameters were relaxed using the conjugated gradient minimization method. The X-ray structures obtained in this study were used as starting points to model the 2 Tz crystal were employed as the starting points. Afterwards, the electronic coupling parameter t 12 was calculated for the different couples of molecules extracted from both the X-ray structures and the modeled crystals.…”