A new type of crown ether. III. Triethylene glycolic diester of naphthalene dithioglycolic acid

Prajer-Janczewski, Lidia; Rudolk, Krystyna; Lis, Tadeusz; Janczewski, Marian; Biskup, J.

doi:10.1139/v83-300

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“…Removal of the solvent and recrystallization from EtOH gave 2.42 g (61%) of pale yellow needles, mp 110-111°C (Lit. 21 mp 110-111°C). 1 H NMR: d = 7.60 (AA'BB', 2 H, ArH), 7.51 (s, 2 H, ArH), 8.04 (AA'BB', 2 H, ArH).…”

Section: 4-diiodonaphthalenementioning

confidence: 99%

Synthesis of Bis(phenylethynyl)arylene-Linked Diporphyrins Designed for Studies of Intramolecular Energy Transfer

Kajanus¹

1999

Synthesis

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A series of donor-bridge-acceptor systems has been designed to give information on how the medium between the donor and the acceptor influences the excitation energy transfer process. The donor and the acceptor are zinc and free base porphyrins, respectively. The systems were obtained by a synthetic strategy that guarantees a precise state of metalation, i.e. by a building block approach in which a third chromophore is formed as the two porphyrins are covalently linked together in a geometrically well defined structure. The porphyrins are linked by one of the three different bridge chromophores; 9,10-bis(phenylethynyl)anthracene, or 1,4-bis(phenylethynyl)-substituted benzene or naphthalene. The different units were assembled using copper-free, palladium-catalyzed cross-coupling of aryl iodides with terminal alkynes. Reference compounds that correspond to different parts of the systems have also been prepared.The preparation of porphyrin arrays is an important area of research, not only for mimicry of different biological processes and elucidation of their mechanisms, but also for the development of molecular electronic devices. In recent years, one of the major tasks has been to prepare arrays of chromophores to probe the electronic communication, i.e. electronic coupling, between the chromophores. Electronic coupling between chromophores is the basis of electron and excitation energy transfer from a donor to an acceptor, 1 two important transfer reactions crucial to natural photosynthesis 2 and molecular devices. 3 The electronic coupling between a donor and an acceptor has been shown to be enhanced by p-conjugated bridges linking donor and acceptor together. 4 However, a systematic study has not yet been reported on how the magnitude of the coupling depends on the energies of the lowest excited states of such a bridge in comparison with corresponding energies of the donor and acceptor. Diporphyrin donor-acceptor systems with large p-conjugated bridges have been prepared and studied with respect to the geometry and distance dependence of the excitation energy or electron transfer. 5In this paper, we report the synthesis of a series of diporphyrin donor-bridge-acceptor (D-B-A) systems designed to give information on how the energetics of the bridge, i.e. the medium between the donor and acceptor, influences excitation energy transfer. In addition to this primary purpose our design of the D-B-A systems was based on two general considerations: ease of preparation and ease of interpretation of photophysical data 6 obtained from the systems. The D-B-A systems were thus given the following features (Figure): The medium between donor (zinc porphyrin) and acceptor (free base porphyrin) was varied by covalently linking the porphyrins together with different bridge chromophores. The tert-butyl groups (I) provide the facial encumbrance necessary for good solubility. The methyl groups in the b position (II) force the planes of the porphyrin and the phenyl ring to be nearly perpendicular and interchromophore conjugation is t...

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Section: 4-diiodonaphthalenementioning

confidence: 99%

Synthesis of Bis(phenylethynyl)arylene-Linked Diporphyrins Designed for Studies of Intramolecular Energy Transfer

Kajanus¹

1999

Synthesis

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A new type of crown ether. III. Triethylene glycolic diester of naphthalene dithioglycolic acid

Abstract: The structure of 2,7-(11,22-diono-12, 15,18.21-tetroxa-9,24-dithia)-hexadecylene-naphthalene was investigated by 1H and 13C nmr and mass spectrometry. An X-ray structural investigation indicated the dissymmetric ansa structure of this compound in the crystalline state.

Cited by 1 publication

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Synthesis of Bis(phenylethynyl)arylene-Linked Diporphyrins Designed for Studies of Intramolecular Energy Transfer

Synthesis of Bis(phenylethynyl)arylene-Linked Diporphyrins Designed for Studies of Intramolecular Energy Transfer

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