Untitled

Fukuda, Takamitsu; Stork, Jay R.; Potucek, Richard J.; Olmstead, Marilyn M.; Noll, Bruce C.; Kobayashi, Nagao; Durfee, William S.

doi:10.1002/1521-3757(20020715)114:14<2677::aid-ange2677>3.0.co;2-z

Cited by 30 publications

(7 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The spectral morphologies of 1 and 2 were almost identical, implying small differences in the frontier orbital energy caused by the manner of connection. This appears similar to those observed for the benzene‐bridged SubPc dimers, but much more blueshifted relative to the Q band of those dimers at approximately 690 nm, owing to the smaller electronic interaction through the pyrene bridge than the benzene bridge. The magnetic circular dichroism (MCD) spectra of 1 and 2 also exhibited similar spectral morphologies with a peak and trough at 546 and 610 nm .…”

Section: Methodssupporting

confidence: 81%

“…Similar to the benzene‐bridged SubPc dimer systems reported independently by Torres et al . and by us, syn and anti isomers ( 1 and 2 ) arising from the manner of connection were obtained along with the pyrene‐fused SubPc monomer 3 and perfluorinated SubPc 4 . The yield of 3 was improved from our previous report under these optimized reaction conditions (see the Supporting Information).…”

Section: Methodsmentioning

confidence: 82%

See 1 more Smart Citation

Pyrene‐Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl‐Shaped π‐Conjugated Systems for Creating Uniquely Curved π‐Conjugated Systems

Nakano

Kage

Furuta

et al. 2016

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

Pyrene-bridged boron subphthalocyanine dimers were synthesized from a mixed-condensation reaction of 2,7-di-tert-butyl-4,5,9,10-tetracyanopyrene and tetrafluorophthalonitrile, and their syn and anti isomers arising from the result of connecting two bowl-shaped boron subphthalocyanine molecules were successfully separated. Expansion of the conjugated system of boron subphthalocyanine through a pyrene bridge caused a redshift of the Q band absorption relative to the parent pyrene-fused monomer, whereas combining the curved π-conjugation of boron subphthalocyanine with the planar π-conjugation of pyrene enabled facile embracement of C60 molecules, owing to the enhanced concave-convex π-π stacking interactions.

show abstract

Section: Methodssupporting

confidence: 81%

Section: Methodsmentioning

confidence: 82%

Pyrene‐Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl‐Shaped π‐Conjugated Systems for Creating Uniquely Curved π‐Conjugated Systems

Nakano

Kage

Furuta

et al. 2016

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the chemistry of subphthalocyanine and subporphyrazine, peripheral fabrications have been widely used for chromophore tuning or attachment of synthetic handles. Taking advantage of versatile phthalonitrile precursors, peripherally halogenated,12a,b arylated, thioalkylated,12c, 13 nitrated,12d and ethynylated14 subphthalocyanines with diverse electronic properties have been synthesized. In contrast, such synthetic procedures are unknown for subporphyrins, and hence the peripheral fabrication reactions reported here are significant and should provide a useful synthetic platform for further functionalizations of subporphyrins.…”

Section: Introductionmentioning

confidence: 99%

Peripheral Hexabromination, Hexaphenylation, and Hexaethynylation of meso‐Aryl‐Substituted Subporphyrins

Tsurumaki

Inokuma

Easwaramoorthi

et al. 2008

Chemistry A European J

View full text Add to dashboard Cite

Effective peripheral fabrication methods of meso-aryl-substituted subporphyrins were explored for the first time. Hexabrominated subporphyrins 2 were prepared quantitatively from the bromination of subporphyrins 1 with bromine. Hexaphenylated subporphyrins 3 and hexaethynylated subporphyrins 4 and 5 were synthesized by Suzuki-Miyaura coupling and Stille coupling, respectively, in good yields. X-ray crystal structures of 2 b, 3 b, 4 b, and 5 a revealed preservation of the bowl-shaped bent structures with bowl depths similar to that of 1. Hexaethynylated subporphyrins exhibit large two-photon-absorption cross-sections due to effective delocalization of the conjugated network to the ethynyl substituents.

show abstract

“…Phthalocyanines are important materials and continue to attract considerable attention because the molecules have a variety of potential applications including use as photosensitizers, catalysts, optical disks, charge-generating materials, and photodynamic therapy. − Unlike porphyrin derivatives, phthalocyanines have the prominent property of exhibiting intense absorption (Q-band) in the near-infrared region. An unadorned phthalocyanine and its metalated derivatives usually exhibit Q-band absorption at around 680 nm.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Phthalocyanines with Eight Benzylchalcogeno Substituents from 5,6-Dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles

et al. 2004

View full text Add to dashboard Cite

Benzo[1,2,3]trichalcogenoles with two bromine atoms on the benzene ring, 5,6-dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles (1a) and (1b) (chalcogen: 1a = S; 1b = Se), were first prepared by treating 2,3,5,6-tetrabromo-1,4-diethylbenzene (TBDEB) with elemental sulfur or amorphous selenium in DBU at 140 degrees C (for 1a) and 100 degrees C (for 1b) for 24 h. The structures of 1a and 1b were verified by NMR spectroscopy, mass spectrometry, and elemental analysis. X-ray crystallographic analysis ultimately showed that the substitution reactions of TBDEB proceeded at the two adjacent bromine atoms. To apply 1a and 1b to construction of phthalocyanine derivatives with sulfur or selenium functional groups, 4,5-bis(benzylchalcogeno)-3,6-diethylphthalonitriles (5a) and (5b) as key intermediates were prepared by way of introduction of alkyl groups (2-cyanoethyl or 4-nitrophenethyl groups) on two chalcogen atoms, substitution of two bromine atoms with nitrile groups, and subsequent exchange of alkyl groups with benzyl groups. Compound 5a was treated with lithium in n-pentanol at 100 degrees C for 1 h to produce 2,3,9,10,16,17,23,24-octakis(benzylthio)-1,4,8,11,15,18,22,25-octaethylphthalocyanine (6a). A similar treatment of 5b in n-hexanol at 100 degrees C for 2 h gave phthalocyanine 6b. The structures of 6a and 6b were determined by (1)H NMR spectroscopy and MALDI-TOFMS. X-ray crystallographic analysis of 6a was also performed. The Q-band absorptions (lambda(max)) for 6a and 6b in UV-vis spectra were observed at 755 nm (log epsilon = 5.1) and 757 nm (log epsilon = 5.1), respectively, and their electrochemical properties were verified by cyclic voltammetry in dichloromethane with Ag/AgNO(3) as a reference electrode. Compounds 6a and 6b were further treated with lithium in THF/NH(3) at -78 degrees C and then with dibutyltin dichloride to produce phthalocyanine derivatives 8a and 8b with four dichalcogenastannole rings by way of octachalcogenate phthalocyanines 7a and 7b.

show abstract

Untitled

Cited by 30 publications

References 6 publications

Pyrene‐Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl‐Shaped π‐Conjugated Systems for Creating Uniquely Curved π‐Conjugated Systems

Pyrene‐Bridged Boron Subphthalocyanine Dimers: Combination of Planar and Bowl‐Shaped π‐Conjugated Systems for Creating Uniquely Curved π‐Conjugated Systems

Peripheral Hexabromination, Hexaphenylation, and Hexaethynylation of meso‐Aryl‐Substituted Subporphyrins

Preparation of Phthalocyanines with Eight Benzylchalcogeno Substituents from 5,6-Dibromo-4,7-diethylbenzo[1,2,3]trichalcogenoles

Contact Info

Product

Resources

About