ChemInform Abstract: Synthesis of Nonsymmetrically Substituted Perylene Fluorescent Dyes.

Kaiser, H.; Lindner, Jörg; Langhals, Heinz

doi:10.1002/chin.199123235

Cited by 6 publications

(7 citation statements)

References 1 publication

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“…The starting compound for the synthesis of 1 is N-heptyloctyl-3,4,9,10-perylenetetracarboxylic-3,4-anhydride-9,10-imide 4. 4 was prepared by partial saponification with potassium hydroxide of the respective symmetric perylene diimide using a method previously described by Langhals, et al (56). The obtained perylene monoimide monoanhydride 4 was condensed in the next step in molten imidazole with zinc acetate as a catalyst with the amine functionality of either Hamilton receptor 5 or 8 to give 1a or 1b, respectively (Fig.…”

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confidence: 99%

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

Grimm

Schornbaum

Jasch

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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In the current work, we have documented the use of two complementary supramolecular motifs, namely multipoint hydrogen bonding and metal complexation, as a means to control the stepby-step assembly of a panchromatically absorbing and highly versatile solar energy conversion system. On one hand, two different perylenediimides (1a/1b) have been integrated together with a metalloporphyrin (2) by means of the Hamilton receptor/cyanuric acid hydrogen bonding motif into energy transduction systems 1a•2 or 1b•2. Steady-state and time-resolved measurements corroborated that upon selective photoexcitation of the perylenediimides (1a/1b), an energy transfer evolved from the singlet excited state of the perylenediimides (1a/1b) to that of the metalloporphyrin (2). On the other hand, fullerene (3) and metalloporphyrin (2) form the electron donor-acceptor system 2•3 via axial complexation. Photophysical measurements confirm that an electron transfer prevails from the singlet excited state of 2 to the electron-accepting 3. The correspondingly formed radical ion pair state decays with a lifetime of 1.0 AE 0.1 ns. As a complement to the aforementioned, the energy transduction features of 1a•2 were combined with the electron donor-acceptor characteristics of 2•3 to afford 1a•2•3. To this end, time-resolved measurements reveal that the initially occurring energy-transfer interaction (53 AE 3 ps) between 1a/1b and 2 is followed by an electron transfer (12 AE 1 ps) from 2 to 3. From multiwavelength analyses, the lifetime of the radical ion pair state in 1a•2•3-as a product of a cascade of light-induced energy and electron transfer-was derived as 3.8 AE 0.2 ns. I n recent years, the conversion of solar energy into electrical energy has been one of the most important areas of scientific research due to the constantly growing human energy demands (1, 2). In order to design efficient, low-cost, environmentally responsible artificial photosynthetic systems, research follows the concepts of nature (3, 4). Similar to natural photosynthetic organisms (5-8), artificial systems undergo cascades of light-induced energy and electron transfer reactions. The absorbed energy is converted into chemical potential energy in the form of a radical ion pair state (9). These events take place in organized arrays of photofunctional chromophores within specifically tailored environments that allow an efficient light harvesting. As an important prerequisite, the lifetime of the excited states should be long enough to power efficient electron transfer in order to obtain radical ion pair states. Therefore, the development of panchromatically absorbing molecules with appropriate absorptive properties for light harvesting is desirable.Owing to their biological relevance and favorable properties as natural chromophores, porphyrinoids are widely used as molecular components in artificial photosynthetic systems. Their functions include panchromatic light harvesting through most of the visible part of the solar spectrum and electron transport (10-26). As another m...

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confidence: 99%

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

Grimm

Schornbaum

Jasch

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

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“…It has been reported that the diimide (structure 4) absorption wavelength and intensity is unaffected by the change of its imide substituents (18,19).…”

Section: Resultsmentioning

confidence: 99%

Positional Effect of Nitrogen Substitution on a Certain Perylene Chromophore-a Semiempirical Treatment

Türker

Gümüş

2008

Polycyclic Aromatic Compounds

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The effect of aza substitution at different sites of a benzimidazole derivative of a perylenetetracarboxylic-3,4,9,10 acid is investigated theoretically. These, as yet nonexistent aza derivatives have been subjected to theoretical analysis at PM3 (RHF) type semiempirical calculations. The results indicate that all the structures are stable but endothermic. Substitution of nitrogen on the bay region of the perylene core is more favored. The electronic and vibrational spectra have also been computed.

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“…Imidazole (RN 288-32-4) and perylene-3,4:9,10-tetracarboxylic bisanhydride were ordered from BASF. Perylene-3,4,9,10-tetracarboxylic-3, 4-anhydride-9,10-(1-hexylheptylimide) was prepared according to the literature [38].…”

Section: Chemicalsmentioning

confidence: 99%

A Sustainable Preparation of Functional Perylenophanes by Domino Metathesis

Langhals¹,

Rauscher²,

Mayer³

2019

GSC

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A sustainable four-step synthesis of soluble perylenophanes for applications as fluorescent optical functional materials is presented and even allows upscaling because of starting with technical bulk products. Thus, terminal alkenylnitriles were alkylated reduced to amines, condensed with perylenetetracarboxylic bisanhydride and cyclised to cyclophanes by means of double cross metathesis in yields until 69% of isolated dyes. The first metathesis by means of the second-generation Hoveyda-Grubbs-catalyst brings the remaining reactive olefinic groups close together favouring the ring-closure to the cyclophanes where the locked neighboring of chromophores in a skew arrangement induce strong exciton interactions. The latter cause an increased the Stokes' separation by means of a moderate hypsochromic shift of light absorption and a stronger bathochromic shift of fluorescence. Various applications such as for lasers, photonics, solar collectors or in analytics are discussed.

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ChemInform Abstract: Synthesis of Nonsymmetrically Substituted Perylene Fluorescent Dyes.

Cited by 6 publications

References 1 publication

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

Step-by-step self-assembled hybrids that feature control over energy and charge transfer

Positional Effect of Nitrogen Substitution on a Certain Perylene Chromophore-a Semiempirical Treatment

A Sustainable Preparation of Functional Perylenophanes by Domino Metathesis

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