Photodehydrocyclizations in stilbene-like compounds—III

Laarhoven, W. H.; Cuppen, T.H.J.H.M.; Nivard, R. J. F.

doi:10.1016/s0040-4020(01)93139-4

Cited by 97 publications

(50 citation statements)

References 11 publications

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“…End-capping agents 1 and 2 (Schemes 1 and 2, respectively) were synthesized as described previously. [20][21][22][23] Instrumentation. Gel permeation chromatograms (GPC) were obtained on an in-house built GPC system using PL Caliber data collection software, three-column set (Polymer Labs, Inc.; 300 × 7.5 mm, 5 µm, 10 -5 , 10 -4 , and 10 -3 Å), with variable UV (IBM model, LC 9563) and RI (Waters 403) detectors.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Thin Film Characterization of Poly(styrene-block-methyl methacrylate) Containing an Anthracene Dimer Photocleavable Junction Point

Goldbach¹,

Russell²,

Penelle³

2002

Macromolecules

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Telechelic high molecular weight polystyrene (PS-A) and poly(methyl methacrylate) (PMMA-A) containing anthracene end groups undergo end-coupling reaction in THF solution to form [4 + 4] anthracene photodimers upon exposure to UV irradiation at wavelengths greater than 300 nm. A mixture of products is obtained that include the coupled polystyrene homopolymer, P(S-AA-S), coupled PMMA homopolymer, P(MMA-AA-MMA), and the desired diblock copolymer, P(S-AA-MMA). The polymer concentration and molecular weights have a direct influence on the photoreaction kinetics but do not affect the molar ratio of the three polymeric products. P(S-AA-MMA), purified by extraction of the homopolymers with selective solvents, exhibits thermal cleavage of the junction points and reversion back to homopolymers at temperatures at or above 135°C. AFM images of thin films of P(S-AA-MMA) spin-coated onto passivated silicon substrates show a microphase-separated cylindrical microdomain morphology with the cylinders oriented normal to the surface.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Thin Film Characterization of Poly(styrene-block-methyl methacrylate) Containing an Anthracene Dimer Photocleavable Junction Point

Goldbach¹,

Russell²,

Penelle³

2002

Macromolecules

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“…1 H NMR spectra were recorded on a Bruker DRX 500 spectrometer (working frequency 500.13 MHz) using Me 4 (10) 1 H NMR spectra were recorded on a Bruker DRX 500 spectrometer (working frequency 500.13 MHz) using Me 4 (10) …”

Section: Methodsmentioning

confidence: 99%

Electrocyclic reaction of crown-containing 2-styrylbenzothiazoles

et al. 2005

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“…Although 29 and 30 were both highly insoluble in most solvents, photocyclization of 29 and 30 was effected in a dilute solution of dioxane to afford a 1: 1 mixture of 2,3,6,7-tetracyanophenanthrene (31) and 2,3,5,6-tetracyanophenanthrene (32) in 60-75% yield (Scheme 4). Regioselectivity in stilbene-like photocyclization reactions can vary, depending on the substituent (30).…”

Section: Bisdicyanoarylethenes From Dicyanoiodoarenesmentioning

confidence: 99%

Multisubstituted phthalonitriles, naphthalenedicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanine syntheses

Leznoff¹,

Terekhov²,

McArthur³

et al. 1995

Can. J. Chem.

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Electrophilic aromatic nitration under mild conditions of 4-hydroxyphthalonitrile gave 4-hydroxy-3-nitrophthalonitrile and 4-hydroxy-5-nitrophthalonitrile, while bromination yielded 3-bromo-4-hydroxyphthalonitrile, 4-bromo-5-hydroxyphthalonitrile, and 3,5-dibromo-4-hydroxyphthalonitrile. Iodination gave 4-hydroxy-5-iodophthalonitrile and 4-hydroxy-3.5-diidophthalonitrile. Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1.2-bis(tri-n-buty1stannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-I ,2-bis(2,3-dicyanophenyl)ethene, and trans-l,2-bis(6,7-dicyanonaphthy1)ethene. Photocyclization of a dilute solution of cis-or trans-I,2-bis(3,4-dicyanopheny1)ethene in dioxane gave a 1: 1 mixture of 2,3,6,7-and 2,3,5,6-tetracyanophenanthrenes separable by chromatography.Key words: phthalonitriles, naphthalenedicarbonitriles, phenanthrenetetracarbonitriles, electrophilic substitution.Resume : La nitration Clectrophile aromatique du 4-hydroxyphtalonitrile, dans des conditions douces, conduit au 4-hydroxy-3-nitrophtalonitrile et au 4-hydroxy-5-nitrophtalonitrile alors que sa bromation fournit du 3-bromo-4-hydroxyphtalonitrile, du 4-bromo-5-hydroxyphtalonitrile, etdu3,5-dibromo-4-hydroxyphtalonitrile. L'iodation foumit du 4-hydroxy-5-iodophtalonitrile et du 4-hydroxy-3.5-diiodophtalonitrile. Le couplage des 4-iodophtalonitrile 3-iodophtalonitrile et 5-iodo-2,3-dicyanonaphtalkne avec du trans-l,2-bis(tri-11-butylstannyl)Cthkne fournit du trans-l,2-bis(3,4-dicyanophCnyl)6thkne, du trans-I ,2-bis(2,3-dicyanophCny1)Cthkne et du trans-1.2-bis(6,7-dicyanonaphty1)Cthkne. La photocyclisation d'une solution diluCe des isomkres cis-et trans-l,2-bis(3,4-dicyanophCny1)tthkne dans le dioxane fournit un melange I : 1 des 2,3,6.7-et 2.3.5.6-tCtracyanophCnanthrknes que l'on peut separer par chromatographie.

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Photodehydrocyclizations in stilbene-like compounds—III

Cited by 97 publications

References 11 publications

Synthesis and Thin Film Characterization of Poly(styrene-block-methyl methacrylate) Containing an Anthracene Dimer Photocleavable Junction Point

Synthesis and Thin Film Characterization of Poly(styrene-block-methyl methacrylate) Containing an Anthracene Dimer Photocleavable Junction Point

Electrocyclic reaction of crown-containing 2-styrylbenzothiazoles

Multisubstituted phthalonitriles, naphthalenedicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanine syntheses

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