Absorption spectroscopy of sandwich dimers and cyclophanes

Ferguson, J.

doi:10.1021/cr00076a001

Cited by 52 publications

(33 citation statements)

References 47 publications

(83 reference statements)

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“…5 % , indicating that the oscillator strength of 2 is approximately twice that of 3. The absence of hypochromism (Desvergne and Bouas-Laurent, 1979;Castellan et al, 1979a, b;Ferguson, 1986) implies the absence of appreciable ground state interaction between the chromophores.…”

Section: Absorption Spectramentioning

confidence: 99%

PHOTOPHYSICS and PHOTOCHEMISTRY OF BIS‐2‐(9‐ANTHRYL)ETHYL GLUTARATE

Fox

Britt

1990

Photochem & Photobiology

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Abstract— The photochemistry and photophysics of bis‐(2‐(9‐anthryl)ethyl glutarate 2 and 2‐(9‐anthryl) ethyl pivalate 3 have been examined as monomeric models for poly‐2‐(9‐anthryl)ethyl methacrylate 1. The absorption and excitation spectra of 2 show no ground state interaction, but appreciable monomer (51%) and excimer (49%) emission. Delayed monomer and excimer fluorescence are also observed in fluid solution at room temperature. Photolysis of 2 at low temperature produces a photoproduct (44% yield) which is unstable at room temperature and presumably is the head‐to‐head (H‐H) dimer. Steady state irradiation of 2 at room temperature (Λ 350 nm) cleanly produces a head‐to‐tail (H‐T) dimer (6) derived from the singlet state and an additional unidentified adduct (7). The product distribution is concentration dependent, with 6 predominating at high concentrations (> 10−3M). The fluorescence spectra of the broken dimers derived from 6 and 7 indicate that substantial ir overlap exists in the transition state leading to each product.

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Section: Absorption Spectramentioning

confidence: 99%

PHOTOPHYSICS and PHOTOCHEMISTRY OF BIS‐2‐(9‐ANTHRYL)ETHYL GLUTARATE

Fox

Britt

1990

Photochem & Photobiology

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“…Cyclophanes with [2.2]linkage are suitable for solving the problem, because the structure is so rigid that there are little conformational changes in the ground and excited states over wide viscosity and temperature ranges [10,11]. Their unique structures make it easy to form p dimers with face-to-face orientations of two aromatic rings.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of local polarity of polymer solids by a rigid fluorescent probe of carbazole–terephthalate cyclophane

Benten

Ohkita

Ito

et al. 2004

Polymer

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“…[3] The absorption intensity of the monomer at approximately l = 320 nm and the subsequent R abs1/abs2 ratio increased with thel igand concentration ( Figure S6 ai nt he Supporting Information), thereby suggesting that the origin of the absorption peak at about l = 320 nm is correspondingt ot he stacking of the two naphthyridine chromophores and the absorption peak at approximately l = 329 nm is due to the characteristic ground electronic state of the monomeric unit. [3] The absorption intensity of the monomer at approximately l = 320 nm and the subsequent R abs1/abs2 ratio increased with thel igand concentration ( Figure S6 ai nt he Supporting Information), thereby suggesting that the origin of the absorption peak at about l = 320 nm is correspondingt ot he stacking of the two naphthyridine chromophores and the absorption peak at approximately l = 329 nm is due to the characteristic ground electronic state of the monomeric unit.…”

Section: Solvent and Concentration Dependency Of The Absorption And Fmentioning

confidence: 99%

“…Cyclophanes [1][2][3][4][5] are ac lass of macrocyclic compounds,w here non-adjacent positions of aromatic units are connectedb ya suitable bridgingunit and spacer group. They have been a subjecto fi nterest due to their unique structure as building blocks and marked chemical properties.…”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of Cyclic Mismatch‐Binding Ligands (CMBLs) with Variable Linkers by Ring‐Closing Metathesis and their Photophysical and DNA Repeat Binding Properties

Mukherjee

Dohno

Nakatani

2017

Chemistry A European J

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Cyclophane-containing bis(2-amino-1,8-naphthyridine) moieties attached to variable linkers at the C2-position (linker B) were synthesized as cyclic mismatch-binding ligands (CMBLs). Ring-closing metathesis (RCM) is used as a key step for the introduction of double bonds at the linker B. Decreasing the size of the linker of the substrate, formation of the RCM products with an increasing trans/cis (E/Z) ratio was observed with moderate to high overall yields. Concentration-dependent fluorescence spectra were observed for CMBLs with longer linkers (n=3), whereas concentration-independent spectra were observed for CMBLs with shorter linkers (n=2 and/or 1) with a marked exception of the E-alkene 6 a. Concomitant changes in the absorption as well as in the fluorescence spectra were also observed for the CMBLs with an increasing hydrophobicity of the solvent. Absorption and fluorescence spectra of the CMBLs in solutions containing 99-100 % methanol resembled to that of the monomer. The binding behavior of these CMBLs with repeat DNA structures was investigated by using a surface plasmon resonance (SPR) assay and circular dichroism (CD) spectra. The cyclic E-alkenes 1 a (n=3) and 3 a (n=2) show an orthogonal binding relationship with d(CCTG) and d(CAG) . However, the selectivity for the cyclic Z-alkenes increased with decreasing the length of the linker from compound 2 b (n=3) to compound 7 b (n=1). These compounds display a large molecular diversity, which allowed the tuning of the binding affinity and selectivity of the CMBLs by varying the linkers towards various biologically significant repeat DNA structures.

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Absorption spectroscopy of sandwich dimers and cyclophanes

Cited by 52 publications

References 47 publications

PHOTOPHYSICS and PHOTOCHEMISTRY OF BIS‐2‐(9‐ANTHRYL)ETHYL GLUTARATE

PHOTOPHYSICS and PHOTOCHEMISTRY OF BIS‐2‐(9‐ANTHRYL)ETHYL GLUTARATE

Evaluation of local polarity of polymer solids by a rigid fluorescent probe of carbazole–terephthalate cyclophane

Design and Synthesis of Cyclic Mismatch‐Binding Ligands (CMBLs) with Variable Linkers by Ring‐Closing Metathesis and their Photophysical and DNA Repeat Binding Properties

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