Synthesis of zincic phthalocyanine derivative functionalized with four peripheral tetrathiafulvalene units

Hu, Yingyu; Shen, Yongjia

doi:10.1002/jhet.5570390535

Cited by 27 publications

(12 citation statements)

References 10 publications

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“…There are numerous reports of Pc derivatives (Chart ) wherein TTF units are attached to the periphery of the macrocyclic core, using either flexible saturated aliphatic linkers (e.g., 71 – 75 ) − or axial coordination to the Pc metal centers (e.g., 76 ) …”

Section: Ttf-annulated Oligopyrrolic Macrocyclic Compoundsmentioning

confidence: 99%

Tetrathiafulvalene- (TTF-) Derived Oligopyrrolic Macrocycles

et al. 2016

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After the epochal discovery of the "organic metal", namely, tetrathiafulvalene (TTF)-7,7,8,8-tetracyano-p-quinodimethane (TCNQ) dyad in 1973, scientists have made efforts to derivatize TTF for constructing various supramolecular architectures to control the charge-transfer processes by adjusting the donor-acceptor strength of the dyads for numerous applications. The interesting inherent electronic donor properties of TTFs control the overall electrochemical properties of the supramolecular structures, leading to the construction of highly efficient optoelectronic materials, photovoltaic solar cells, organic field-effect transistors, and optical sensors. Modified TTF structures thus constitute promising candidates for the development of so-called "functional materials" that could see use in modern technological applications. The versatility of the TTF unit and the pioneering synthetic strategies that have been developed over the past few decades provide opportunities to tune the architecture and function for specific purposes. This review covers the "state of the art" associated with TTF-annulated oligopyrrolic macrocyclic compounds. Points of emphasis include synthesis, properties, and potential applications.

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Section: Ttf-annulated Oligopyrrolic Macrocyclic Compoundsmentioning

confidence: 99%

Tetrathiafulvalene- (TTF-) Derived Oligopyrrolic Macrocycles

et al. 2016

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“…0.014 mmol/L). Acetic acid 2-(4,5-Bis-hexylsulfanyl [1,3]dithiol-2-ylidene)-tetrahydro [1,3]dithiolo [4,5-b] [1,4]dithiin-5-yl propyl ester, compound 1, was prepared according to the method introduced [13]. [1,3]dithiol-2-ylidene)-tetrahydro [1,3]dithiolo [4,5-b] [1,4]dithiin-5-yl]-propanol (2) A total of 0.91 g (16.2 mmol) potassium hydroxide dissolved in 65 mL methanol was added dropwise to the mixture of 2.61 g (4.2 mmol) (1) and 22 mL chloroform with stirring.…”

Section: Generalmentioning

confidence: 99%

“…J values were in Hz. 13 C NMR spectra were obtained on a Bruker ADVANCE 500 spectrometer operating at 125.76 MHz. UV/VIS spectra were recorded on a SHIMADZU UV365 spectrophotometer.…”

Section: Generalmentioning

confidence: 99%

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Synthesis, optical spectroscopy and electrochemistry of TTF-derived metallophthalocyanine complexes

Lai

Shen

et al. 2005

Dyes and Pigments

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“…f) P(OEt) 3 [24], which was immediately converted into the Zn II complex 21 (60% yield; Scheme 6). Subsequent alkylation with hexyl bromide [25] afforded dithiolthione 22, which was transformed with Hg(OAc) 2 into the desired dithiolone 20. P(OEt) 3 -Mediated coupling of macrocyclic dithiolthione 18 with 20 (6 equiv.)…”

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confidence: 99%

Tetrathiafulvalene (TTF)-Bridged Resorcin[4]arene Cavitands: Towards New Electrochemical Molecular Switches

Frei

Diederich

Tremont

et al. 2006

HCA

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We report the synthesis of novel resorcin [4]arene-based cavitands featuring two extended bridges consisting of quinoxaline-fused TTF (tetrathiafulvalene) moieties. In the neutral form, these cavitands were expected to adopt the vase form, whereas, upon oxidation, the open kite geometry should be preferred due to Coulombic repulsion between the two TTF radical cations (Scheme 2). The key step in the preparation of these novel molecular switches was the P(OEt) 3 -mediated coupling between a macrocyclic bis(1,3-dithiol-2-thione) and 2 equiv. of a suitable 1,3-dithiol-2-one. Following the successful application of this strategy to the preparation of mono-TTF-cavitand 3 (Scheme 3), the synthesis of the bis-TTF derivatives 2 (Scheme 4) and 19 (Scheme 5) was pursued; however, the target compounds could not be isolated due to their insolubility. Upon decorating both the octol bowl and the TTF cavity rims with long alkyl chains, the soluble bis-TTF cavitand 23 was finally obtained, besides a minor amount of the novel cage compound 25a featuring a highly distorted TTF bridge (Scheme 6). In contrast to 25a, the deep cavitand 23 undergoes reversible vase ! kite switching upon lowering the temperature from 293 to 193 K (Fig. 1). Electrochemical studies by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) provided preliminary evidence for successful vase ! kite switching of 23 induced by the oxidation of the TTF cavity walls. The vase conformer is prevalent at room temperature at neutral pH, whereas the kite geometry is predominant at low temperatures ( 213 K) [1], upon protonation with acids such as CF 3 COOH (TFA) [4], or in the presence of Zn II ions [5]. At low temperature, solvation of the more extended surface stabilizes the kite geometry, whereas, at higher temperature, the entropic term TDS solv becomes unfavorable, and the vase conformation is dominant [1]. More recent investigations also showed that suitably sized solvent molecules (such as small benzene derivatives) favorably solvate (stabilize) the vase form and reduce the propensity for vase ! kite transition [6]. On the other hand, the kite conformation is additionally stabilized by solvents with substantial H-bonding acidity: weak H-bonding interactions between the mildly basic quinoxaline N-atoms, and solvent molecules are more efficient in the open kite than in the closed vase form [6b]. Acid-induced switching from the vase to the kite

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Synthesis of zincic phthalocyanine derivative functionalized with four peripheral tetrathiafulvalene units

Cited by 27 publications

References 10 publications

Tetrathiafulvalene- (TTF-) Derived Oligopyrrolic Macrocycles

Tetrathiafulvalene- (TTF-) Derived Oligopyrrolic Macrocycles

Synthesis, optical spectroscopy and electrochemistry of TTF-derived metallophthalocyanine complexes

Tetrathiafulvalene (TTF)-Bridged Resorcin[4]arene Cavitands: Towards New Electrochemical Molecular Switches

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