A simple way to sequentially connected polycycles containing terminal pyrrole rings: synthesis of possible precursors of materials for nonlinear optics

Lucchesini, Francesco

doi:10.1016/s0040-4020(01)92285-9

Cited by 36 publications

(24 citation statements)

References 32 publications

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“…The latter combine high electrical conductivity, with thermal and environmental stability. [17][18][19][20][21][22][23][24][25][26][27][28][29] In the last few years donor substituted tricyanovinyl compounds have received a lot of interest. Due to their strong solvatochromic properties, which mainly originate from their donoracceptor substitution, they can be used as model compounds for dyes with strong NLO properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

et al. 2005

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-Tricyanovinyl-substituted 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 1 have been synthesized by direct tricyanovinylation reaction of 1-(alkyl)aryl-2-(2´-thienyl)pyrroles 2 using TCNE. The tricyanovinyl-derivatives 1 display dramatic reductions in both their optical and electrochemical band gaps relative to thienylpyrrole precursors 2. The solvatochromic behavior of compounds 1 was investigated in a variety of solvents. Hyper-Rayleigh scattering was used to measure the first hyperpolarizabilities β of the mentioned compounds. The β values show that the new compounds prepared could be used on the manufacture of materials with good non-linear (NLO) properties.

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Section: Introductionmentioning

confidence: 99%

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

et al. 2005

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“…The very useful methodology of Route 2 (Scheme 2) was modeled after work done by Lucchesini [9]. 9,9-Dihexadecylfluorene (5) after reaction with BuLi was immediately reacted with two equivalents of 1,3-dioxolane-2-propanal to give the dioxolanol derivative, which was used without purification in the next step.…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, we chose to use a variation of Lucchesini [9] approach in large scale preparation. Novel compounds were characterized by 1 H NMR and 13 C NMR.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Design and Electrochemical Properties of Langmuir–Blodgett (LB) Films Built of Bis(Pyrrolyl)Fluorene

et al. 2006

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The synthesis, characterization, electropolymerization, electrical and sensing properties of LB films of mono-and dihexadecyl-bis(pyrrolyl)fluorene derivatives are reported. Different responses to different gases at various concentrations obtained for mono-and disubstituted derivatives of bis(pyrrolyl)fluorene make these materials a very good candidates for elements of gas sensing devices of the different type of an "artificial nose" or a neuronic network.

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“…The subsequent Suzuki reaction with the pyrrole boronic acid, 46 according to the optimized conditions for the arylation with pyrrole 47 and the Boc-deprotection in basic conditions (Scheme 1) gave the target compound 2. 48 Scheme 1. The synthetic strategy for para-derivative 4 was different than for 2 and 3 since bromide 8 was not prepared in a metal-catalyzed cross-coupling.…”

Section: Synthesismentioning

confidence: 99%

Phototautomerization in Pyrrolylphenylpyridine Terphenyl Systems

et al. 2015

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[4-(2-Pyrrolyl)phenyl]pyridines 2-4 were synthesized and their photophysical properties and reactivity in phototautomerization reactions investigated by fluorescence spectroscopy and laser flash photolysis (LFP). The pKa for the protonation of the pyridine nitrogen in 2-4 was determined by UV-vis and fluorescence titration (pKa = 5.5 for 4). On excitation in polar protic solvents, 2-4 populate charge-transfer states leading to an enhanced basicity of the pyridine (pKa* ≈ 12) and enhanced acidity of pyrrole (pKa* ≈ 8-9) enabling excited-state proton transfer (ESPT). ESPT gives rise to phototautomers and significantly quenches the fluorescence of 2-4. Phototautomers 2-T and 4-T were detected by LFP with strong transient absorption maxima at 390 nm. Phototautomers 2-T and 4-T decayed by competing uni- and bimolecular reactions. However, at pH 11 the decay of 4-T followed exponential kinetics with a rate constant of 4.2 × 10(6) s(-1). The pyridinium salt 4H(+) forms a stable complex with cucurbit[7]uril (CB[7]) with 1:1 stoichiometry (β11 = (1.0 ± 0.2) × 10(5) M(-1), [Na(+)] = 39 mM). Complexation to CB[7] increased the pKa for 4H(+) (pKa = 6.9) and changed its photochemical reactivity. Homolytic cleavage of the pyrrole NH leads to the formation of an N-radical because of the decreased acidity of the pyrrole in the inclusion complex.

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A simple way to sequentially connected polycycles containing terminal pyrrole rings: synthesis of possible precursors of materials for nonlinear optics

Cited by 36 publications

References 32 publications

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Synthesis of tricyanovinyl-substituted thienylpyrroles and characterization of the solvatochromic, electrochemical and non-linear optical properties

Synthesis, Design and Electrochemical Properties of Langmuir–Blodgett (LB) Films Built of Bis(Pyrrolyl)Fluorene

Phototautomerization in Pyrrolylphenylpyridine Terphenyl Systems

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