Ein Biphenylenylendiporphyrin: Zwei cofacial angeordnete Porphyrine mit Biphenylenbrücke

Chang, C. K.; Abdalmuhdi, I.

doi:10.1002/ange.19840960221

Cited by 23 publications

(11 citation statements)

References 13 publications

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“…Materials: H 2 P, H 4 DPS, [12] H 4 DPX, [39] H 4 DPB, [61] and their metalated derivatives [12,34,39,41,62] were synthesized by using methods reported in the literature. Unless otherwise stated, all reagents and solvents were used as received.…”

Section: Methodsmentioning

confidence: 99%

Triplet–Triplet Energy Transfer Controlled by the Donor–Acceptor Distance in Rigidly Held Palladium‐Containing Cofacial Bisporphyrins

Faure

Stern

Espinosa

et al. 2005

Chemistry A European J

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Eleven new complexes, including mono-, heterobi-, and homobimetallic cofacial bisporphyrins, (Pd)H2DPS, (M)H2DPX, (M)H2DPB, (PdZn)DPS, (PdZn)DPX, (Pt)2DPX, (M)2DPB (M = Pd, Pt), and (Pt)P (DPS4- = 4,6-bis[5-(2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrinyl)]dibenzothiophene tetraanion, DPX(4-) = 4,5-bis[5-(2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrinyl)]-9,9-dimethylxanthene tetraanion, DPB4- = 1,8-bis[5-(2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrinyl)]biphenylene tetraanion, P2- = 5-phenyl-2,8,13,17-tetraethyl-3,7,12,18-tetramethylporphyrin dianion) have been synthesized and characterized. The photophysical properties of the donor (M)P (M=Pd or Pt, P=porphyrin chromophore) and the acceptor (free base H(2)P or (Zn)P) depend on the C(meso)-C(meso) distance and the presence of a heavy atom such as Pd(II) or Pt(II). The data were compared with those for the known compounds (Pd)2DPS, (Pd)2DPX, H4DPS, H4DPX, H4DPB, (Pd)P, (Zn)P, and H(2)P. The rate constants for triplet-triplet energy transfer (k(ET)) were measured for the heterobimetallic (PdZn) and monometallic [(M)H2] derivatives (M=Pd, Pt). The fluorescence lifetimes (Deltatau(F)) of the acceptors decrease as a result of the heavy-atom effect, and vary as follows: (Pd)H2DPS<<(Pd)H2DPX approximately (Pd)H2DPB. The k(ET) values calculated according to the equation k(ET)=(1/tau(emi)-1/tau(emi) (0)), where tau(emi) (0) is the emission lifetime of the homobimetallic bisporphyrins (no ET occurs), are equal to 0, 247+/-57 and 133+/-52 s(-1) for DPS, DPX, and DPB, respectively, in the (Pd)H(2) series. These measurements allowed the range of distance over which the Dexter mechanism for T(1)-T(1) energy transfer ceases to operate to be determined. This distance is somewhere between 4.3 and 6.3 A, in agreement with our recent findings on singlet-singlet energy transfer. During the course of this study, the X-ray crystal structure for (Pd)H2DPX was obtained; triclinic (P1), a = 11.1016(1), b = 14.9868(2), c = 20.6786(3) A, alpha = 102.091(1), beta = 100.587(1), gamma = 101.817(1) degrees , V = 3199.19(7) A(3), Z = 2.

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Section: Methodsmentioning

confidence: 99%

Triplet–Triplet Energy Transfer Controlled by the Donor–Acceptor Distance in Rigidly Held Palladium‐Containing Cofacial Bisporphyrins

Faure

Stern

Espinosa

et al. 2005

Chemistry A European J

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“…

Porphyrins are widely used for functional molecular systems based on their excellent photophysical and redox properties. [2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds. [2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds.

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confidence: 99%

“…The solvent was chosen for the good solubility of both 1 and the complexes. ESI-MS measurements of the sample gave a set of signals assigned to the porphyrin dimer [Ag 4 The 1 H NMR spectrum showed that 1 adopted a C 4 symmetry in the complex.…”

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confidence: 99%

“…H NMR signals of the intercalated 3 of [3&2](OTf)4 were observed at d = 3.57, 3.04, and 2.31 ppm, which were significantly upfield shifted (Dd = À4.35 to À6.06 ppm) compared to those in the absence of 2 4+ . This result indicates that the protons of the intercalated 3 were positioned between the two Zn-porphyrin rings of 2 4+ and therefore remarkably affected by the shielding effect.…”

mentioning

confidence: 99%

“…[1] In particular, multiple porphyrins arranged in a well-ordered manner show unique functions such as photoelectron conversion, catalysis, and molecular recognition, all of which cannot be achieved by a monomeric porphyrin analogue. [2,3] Cofacial porphyrin dimers can be readily constructed by linking two porphyrin rings by covalent, [4][5][6][7][8][9][10][11][12] hydrogen, [13] or coordination bonds. [14][15][16][17][18][19] So far, a great number of porphyrin dimers have been reported as host molecules for guest recognition.…”

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confidence: 99%

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Silver‐Mediated Formation of a Cofacial Porphyrin Dimer with the Ability to Intercalate Aromatic Molecules

2013

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Guests welcome: Complex formation between AgI ions and a Zn‐porphyrin ligand (L) possessing four 2,2′‐bipyridyl groups produced a dimeric complex [Ag4L2]4+, wherein the interplane distance between the Zn‐porphyrin groups was ideal for intercalation of aromatic molecules through π–π interactions. The cofacial dimer [Ag4L2]4+ serves as an excellent receptor for π‐electron‐deficient guests.

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Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

Iyoda

2009

Adv Synth Catal

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Efficient methods for the syntheses of biaryls by the copper-mediated homocoupling of arylmetals are summarized. First, a smooth transmetallation between arylzinc halides and copper(II) salts has been employed for the selective homocoupling of arylzinc halides to produce either biphenylenes or tetraphenylenes. This reaction has been applied to the synthesis of cyclic oligothiophenes. Second, an efficient method for the homocoupling of aryl halides by the electron-transfer (ET) oxidation of Lipshutz cuprates [Ar 2 Cu(CN)Li 2 ] with organic electron acceptors has been developed. The ET oxidation of cuprates with 1,4-benzoquinones proceeds smoothly to afford the corresponding coupling products in moderate to high yields. The ET oxidation of cuprates has been applied to the synthesis of either thiophene-or benzene-fused 10-membered ring cyclophanes. For the synthesis of macrocyclic cyclophanes, a linear C À Cu À C structure of Lipshutz cuprates should be maintained in the dimetallacyclic intermediates to efficiently produce large-ring cyclophanes. Moreover, nonaphenylenes and dodecaphenylenes have been synthesized using the ET oxidation of cuprates with duroquinone. Interestingly,

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Ein Biphenylenylendiporphyrin: Zwei cofacial angeordnete Porphyrine mit Biphenylenbrücke

Cited by 23 publications

References 13 publications

Triplet–Triplet Energy Transfer Controlled by the Donor–Acceptor Distance in Rigidly Held Palladium‐Containing Cofacial Bisporphyrins

Triplet–Triplet Energy Transfer Controlled by the Donor–Acceptor Distance in Rigidly Held Palladium‐Containing Cofacial Bisporphyrins

Silver‐Mediated Formation of a Cofacial Porphyrin Dimer with the Ability to Intercalate Aromatic Molecules

Copper‐Mediated Aryl‐Aryl Couplings for the Construction of Oligophenylenes and Related Heteroaromatics

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