A Linear Multiporphyrinic [2]-Rotaxane via Amide Bond Formation

Blanco, María-Jesús; Chambron, Jean‐Claude; Heitz, Valérie; Sauvage, Jean‐Pierre

doi:10.1021/ol006137b

Cited by 38 publications

(15 citation statements)

References 17 publications

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“…The porphyrin-tethering wheel 2(H 2 ) was prepared from a crown ether derivative 13 [27] and a aminoporphyrin derivative 14 [28] (Scheme 2). Its zinc complex 2(Zn) was obtained in 96% yield by reaction with Zn(OAc) 2 .…”

Section: Resultsmentioning

confidence: 84%

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Photoinduced electron transfer processes in three component rotaxanes with porphyrins, [60]fullerene and triphenylamine

Sasabe

Furusho

Sandanayaka

et al. 2006

J. Porphyrins Phthalocyanines

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Electron transfer processes occurring through-space and through-bond were studied for novel mechanically linked triad [2]rotaxanes, which contain a porphyrin (MP) unit as a pendant and [60]fullerene (C 60 ) and triphenylamine (TPA) moieties as stopper groups at the axle ends (abbreviated as (MP;C 60 -TPA) rot+ with MP = H 2 P or ZnP. The photophysical properties were investigated by means of time-resolved fluorescence and transient absorption measurements with changing solvent polarity. The charge separation took place mainly via ( 1 MP*;C 60 -TPA) rot+ and (MP; 1 C 60 *-TPA) rot+ in polar solvents. Within the charge-separated states of triads (MP;C 60 -TPA) rot+ , hole-shift and/or back electron transfer took place competitively. The lifetime of the charge separation state of (ZnP;C 60 -TPA) rot+ was similar to that of dyad (C 60 -TPA) rot+ (140 ns in dimethylformamide), whereas that of (H 2 P;C 60 -TPA) rot+ was as long as 230 ns, suggesting two final charge separation states such as (MP;C 60•--TPA •+ ) rot+ and (MP •+ ;C 60•--TPA) rot+ depending on the kind of porphyrin.

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Section: Resultsmentioning

confidence: 84%

“…For preparative high performance liquid chromatography (HPLC), a JAICO LC-908 system using columns JAIGEL 1 and 2 was employed. Compounds 5, 6, 11, 13 and 14 were prepared according to the methods described in the literature [22][23][24][25][26][27][28].…”

Section: Methodsmentioning

confidence: 99%

Photoinduced electron transfer processes in three component rotaxanes with porphyrins, [60]fullerene and triphenylamine

Sasabe

Furusho

Sandanayaka

et al. 2006

J. Porphyrins Phthalocyanines

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“…The synthesis of the copper-coordinated pseudorotaxanate [1·Cu]·PF 6 and the subsequent preparation of MOF-1040 employing this strut are summarized in Scheme 1. The [2]pseudorotaxanate [1·Cu]·PF 6 was prepared through the effective Cu I -templated "gathering-and-threading" approach [5a,b] of a copper(I) catenate by 1) mixing of 2·HCl [6] with Et 3 N, thus generating the dicarboxylate of 2, followed by 2) the addition of the copper complex [7] of 3, which was prepared by 3) the reaction of the coordinating ring with [Cu(CH 3 CN) 4 ]PF 6 in stoichiometric amounts, followed by 4) reprotonation of the dicarboxylate and counterion exchange with saturated aqueous NH 4 PF 6 solution, resulting in the production of [1·Cu]·PF 6 in 87 % yield.…”

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confidence: 99%

“…Mixing [1·Cu]·PF 6 and Zn(NO 3 ) 2 ·6 H 2 O in diethylformamide (DEF) at 100 8C in a sealed tube for 48 h resulted (see Experimental Section) in the formation of red cubic crystals of MOF-1040. The single-crystal X-ray diffraction study was performed using synchrotron radiation in the beamline 24-ID-C at NECAT, in the Advanced Photon Source (APS) at Argonne National Laboratory.…”

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confidence: 99%

Metal–Organic Frameworks Incorporating Copper‐Complexed Rotaxanes

et al. 2012

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“…[46,47] A target free-base Por-Fl-linked dyad (H 2 PorÀFl, 2À H 2 ) was prepared from 1ÀH 2 through a four-step synthesis that was a general synthetic route for Fl derivatives: [48] reduction of the nitro group, coupling with 2-bromonitrobenzene, reduction of the nitro group, and formation of the isoalloxazine ring (Scheme 1). Insertion of the Pd 2 + ion into the Por core was made by the reaction of the mononitroporphyrin with Pd(OAc) 2 in toluene.…”

Section: Resultsmentioning

confidence: 99%

Binding of Scandium Ions to Metalloporphyrin–Flavin Complexes for Long‐Lived Charge Separation

Kojima

Kobayashi

Ishizuka

et al. 2014

Chemistry A European J

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A porphyrin-flavin-linked dyad and its zinc and palladium complexes (MPor-Fl: 2-M, M=2 H, Zn, and Pd) were newly synthesized and the X-ray crystal structure of 2-Pd was determined. The photodynamics of 2-M were examined by femto- and nanosecond laser flash photolysis measurements. Photoinduced electron transfer (ET) in 2-H2 occurred from the singlet excited state of the porphyrin moiety (H2 Por) to the flavin (Fl) moiety to produce the singlet charge-separated (CS) state (1) (H2 Por(.+) -Fl(.-) ), which decayed through back ET (BET) to form (3) [H2 Por]*-Fl with rate constants of 1.2×10(10) and 1.2×10(9) s(-1) , respectively. Similarly, photoinduced ET in 2-Pd afforded the singlet CS state, which decayed through BET to form (3) [PdPor]*Fl with rate constants of 2.1×10(11) and 6.0×10(10) s(-1) , respectively. The rate constant of photoinduced ET and BET of 2-M were related to the ET and BET driving forces by using the Marcus theory of ET. One and two Sc(3+) ions bind to the flavin moiety to form the Fl-Sc(3+) and Fl-(Sc(3+) )2 complexes with binding constants of K1 =2.2×10(5) M(-1) and K2 =1.8×10(3) M(-1) , respectively. Other metal ions, such as Y(3+) , Zn(2+) , and Mg(2+) , form only 1:1 complexes with flavin. In contrast to 2-M and the 1:1 complexes with metal ions, which afforded the short-lived singlet CS state, photoinduced ET in 2-Pd⋅⋅⋅Sc(3+) complexes afforded the triplet CS state ((3) [PdPor(.+) -Fl(.-) (Sc(3+) )2 ]), which exhibited a remarkably long lifetime of τ=110 ms (kBET =9.1 s(-1) ).

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A Linear Multiporphyrinic [2]-Rotaxane via Amide Bond Formation

Cited by 38 publications

References 17 publications

Photoinduced electron transfer processes in three component rotaxanes with porphyrins, [60]fullerene and triphenylamine

Photoinduced electron transfer processes in three component rotaxanes with porphyrins, [60]fullerene and triphenylamine

Metal–Organic Frameworks Incorporating Copper‐Complexed Rotaxanes

Binding of Scandium Ions to Metalloporphyrin–Flavin Complexes for Long‐Lived Charge Separation

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