Optical Processing with Photochromic Switches

Raymo, Françisco M.; Tomasulo, Massimiliano

doi:10.1002/chem.200501178

Cited by 180 publications

(82 citation statements)

References 43 publications

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“…The potential application of these components in optical and electronic memory devices has attracted considerable effort to this research area. [2] Of particular interest is the design of fluorescent molecular switches, as they can precisely control the fluorescence properties by simple chemical input, even down to the level of single molecules or ions under ambient conditions.…”

Section: Introductionmentioning

confidence: 99%

A Fluorescent Molecular Switch Driven by the Input Sequence of Metal Cations: An Azamacrocyclic Ligand Containing Bipolar Anthracene Fragments

Nishimura¹,

Maehara²,

Shiraishi³

et al. 2007

Chemistry A European J

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An azamacrocyclic ligand (L) containing two anthracene (AN) fragments connected through two triethylenetetramine bridges has been synthesized, in which each of the bridges can coordinate with one metal cation. The effects of pH and metal cations (Zn2+ and Cd2+) on the emission properties of L were studied in water. Without metal cations, L does not show any emission at basic pH values. The addition of Zn2+ leads to the production of excimer emission, which is due to a static excimer formed by direct excitation of the intramolecular ground-state dimer of the bipolar AN fragments that approach each other by Zn2+ binding. In contrast, Cd2+ addition does not result in excimer emission because the Cd2+-AN pi complex, formed by donation of a pi electron of the AN fragments to the adjacent Cd2+, suppresses pi-stacking interactions of the AN fragments. The most notable feature is the appearance of excimer emission controlled by the input sequence of metal cations: Zn2+-->Cd2+ sequential addition (each one equivalent) allows excimer emission, whereas the reverse sequence (Cd2+-->Zn2+) does not. In the Zn2+-->Cd2+ sequence, Cd2+ coordination is structurally restricted by the first Zn2+ coordination with the other polyamine bridge, leading to the formation of a weak Cd2+-AN pi complex. In contrast, for the reverse sequence, the first Cd2+ coordination forms a stable Cd2+-AN pi complex, which is not weakened by sequential Zn2+ coordination, resulting in no excimer emission.

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Section: Introductionmentioning

confidence: 99%

A Fluorescent Molecular Switch Driven by the Input Sequence of Metal Cations: An Azamacrocyclic Ligand Containing Bipolar Anthracene Fragments

Nishimura¹,

Maehara²,

Shiraishi³

et al. 2007

Chemistry A European J

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“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Some time ago we found a seco-cyclo isomerism which is based on the reversible intramolecular [4π+4π]photocycloaddition of benzene rings to anthracene. [16] The utility of such a system depends strongly on clean switching processes in both directions.…”

Section: Introductionmentioning

confidence: 99%

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

et al. 2007

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“…[2,3] A number of molecular switches and logic gates based on SP derivatives are reported. [4][5][6][7][8][9][10] Meanwhile, assemblies of SP compounds and relevant photomodulation have also attracted attention. In the 1970's, Krongauz et al reported the formation of MC aggregates (referred to as ''quasicrystals'') upon UV irradiation of SP molecules in aliphatic hydrocarbons.…”

Section: Introductionmentioning

confidence: 99%

Light‐Triggered Self‐Assembly of a Spiropyran‐Functionalized Dendron into Nano‐/Micrometer‐Sized Particles and Photoresponsive Organogel with Switchable Fluorescence

Chen

Zhang

et al. 2009

Adv Funct Materials

123

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The synthesis, self‐assembly, and spectroscopic investigations of spiropyran (SP)‐functionalized dendron 1 are reported. Under UV light irradiation, assembly of 1 into nano‐/microparticles occurs due to the transformation of the closed form of SP into the open merocyanine (MC) form. The formation of these nano‐/microparticles is confirmed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) experiments in addition to the confocal laser scanning microscopy (CLSM) measurements. These nano‐/microparticles exhibit relatively strong red emission. It is interesting to note that the direct cooling of the toluene/benzene solution of 1 to 0 °C leads to gel formation. Multivalent π–π interactions due to the dendron in 1 may be the driving‐force for the gelation. The UV light irradiation cannot destroy the gel phase, and in fact, the gel–gel transition is successfully realized. The purple‐blue gel exhibits relatively strong red fluorescence; moreover, the fluorescence can be reversibly switched by alternating UV and visible light irradiation. The results clearly indicate that the MC form after aggregation becomes more stable and fluorescent.

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Optical Processing with Photochromic Switches

Cited by 180 publications

References 43 publications

A Fluorescent Molecular Switch Driven by the Input Sequence of Metal Cations: An Azamacrocyclic Ligand Containing Bipolar Anthracene Fragments

A Fluorescent Molecular Switch Driven by the Input Sequence of Metal Cations: An Azamacrocyclic Ligand Containing Bipolar Anthracene Fragments

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

Light‐Triggered Self‐Assembly of a Spiropyran‐Functionalized Dendron into Nano‐/Micrometer‐Sized Particles and Photoresponsive Organogel with Switchable Fluorescence

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