Water-Soluble Paracyclophane Fluorophores with Large Two-Photon Action Cross Sections

2005 ◽  
Vol 871 ◽  
Author(s):  
Han Young Woo ◽  
Dmitry Korystov ◽  
Alexander Mikhailovsky ◽  
Guillermo C. Bazan
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Solvent Polarity ◽  
Water Soluble ◽  
Photon Absorption ◽  
Significant Drop ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Donor Ability ◽  
Fine Tune

AbstractA series of tetradonor substituted [2.2]paracyclophane-based two-photon absorption (TPA) fluorophores were designed, synthesized and characterized. Different substituents were chosen to modulate the conjugation and the donor strength and to allow the molecules to be neutral (N series, organic-soluble) or charged (C series, water-soluble). The overall set of compounds series allows us to examine the correlation among the solvent polarity, donor ability of the substituents, and TPA action cross section (ηδd, where δ is the TPA cross section and η is the quantum yield). In water, a significant drop of both δ and η is observed, approximately one-third relative to those in toluene. Weaker donors and/or weaker acceptors with enhanced conjugation are a better choice due to a minimized quenching related to strong charge transfer (CT) upon excitation. One thus needs to fine-tune the magnitude of CT and find an optimal balance among CT,δ and η.

Syntheses and properties of acetylene-linked bis- and trisporphyrins toward two-photon photodynamic therapy

2007 ◽  
Vol 11 (06) ◽  
pp. 406-417 ◽  
Author(s):  
Yusuke Inaba ◽  
Kazuya Ogawa ◽  
Yoshiaki Kobuke
Keyword(s):  
Photodynamic Therapy ◽  
Cross Section ◽  
Sodium Salt ◽  
Absorption Cross Section ◽  
Water Soluble ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Two Photon Absorption ◽  
Photon Irradiation ◽  
Two Photon

Acetylene-bridged bisporphyrins and trisporphyrins having branched bulky bis(carboxylethyl)methyl meso-substituents were synthesized. These compounds showed large effective two-photon absorption cross-section values at 890 nm measured by using a nanosecond Z-scan method. Sodium salt of hydrolyzed trisporphyrins showed broad and red-shifted Q-bands over 900 nm. Two-photon absorption cross-section values of water-soluble dimers in water were similar to, or slightly larger than, those of ester forms evaluated in toluene. Furthermore, the generation of singlet oxygen upon one-photon irradiation for dimers in water was confirmed.

A small-molecule with a large two-photon absorption cross-section serves as a membrane-permeable ribonucleic acid (RNA) probe for live cell imaging

2018 ◽  
Vol 42 (17) ◽  
pp. 14325-14331 ◽  
Author(s):  
Ruiqing Feng ◽  
Longlong Li ◽  
Bing Li ◽  
Jinhui Li ◽  
Dan Peng ◽  
...  
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Live Cell Imaging ◽  
Plasma Membranes ◽  
Cell Imaging ◽  
Photon Absorption ◽  
Absorption Cross ◽  
High Permeability ◽  
Two Photon Absorption ◽  
Two Photon

DMI could light up the RNA of the nucleus and the cytoplasm in living systems, which not only exhibits larger two-photon absorption cross-sections (981 GM), but also displays high-permeability to plasma membranes of vigorous cells.

scholarly journals Ultrafast processes triggered by one- and two-photon excitation of a photochromic and luminescent hydrazone

2019 ◽  
Vol 15 ◽  
pp. 2438-2446 ◽  
Author(s):  
Alessandro Iagatti ◽  
Baihao Shao ◽  
Alberto Credi ◽  
Barbara Ventura ◽  
Ivan Aprahamian ◽  
...  
Keyword(s):  
Excited State ◽  
Cross Section ◽  
Absorption Cross Section ◽  
Transient Absorption ◽  
Solvent Polarity ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Time Resolved ◽  
Two Photon Absorption ◽  
Two Photon

In this work we apply a combination of steady state and time resolved luminescence and absorption spectroscopies to investigate the excited-state dynamics of a recently developed molecular photoswitch, belonging to the hydrazone family. The outstanding properties of this molecule, involving fluorescence toggling, bistability, high isomerization quantum yield and non-negligible two-photon absorption cross section, make it very promising for numerous applications. Here we show that the light induced Z/E isomerization occurs on a fast <1 ps timescale in both toluene and acetonitrile, while the excited state lifetime of the Z-form depends on solvent polarity, suggesting a partial charge transfer nature of its low lying excited state. Time-resolved luminescence measurements evidence the presence of a main emission component in the 500–520 nm spectral range, attributed to the Z-isomer, and a very short living blue-shifted emission, attributed to the E-isomer. Finally, transient absorption measurements performed upon far-red excitation are employed as an alternative method to determine the two-photon absorption cross-section of the molecule.

Water-Soluble Bis(imidazolylporphyrin) Self-Assemblies with Large Two-Photon Absorption Cross Sections as Potential Agents for Photodynamic Therapy

2006 ◽  
Vol 49 (7) ◽  
pp. 2276-2283 ◽  
Author(s):  
Kazuya Ogawa ◽  
Hideki Hasegawa ◽  
Yusuke Inaba ◽  
Yoshiaki Kobuke ◽  
Hideyuki Inouye ◽  
...  
Keyword(s):  
Photodynamic Therapy ◽  
Cross Sections ◽  
Water Soluble ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Two Photon Absorption ◽  
Two Photon

scholarly journals Small water-soluble pyrimidine hexafluorophosphate derivatives with high two-photon absorption activities in the near-IR region and their biological applications

RSC Advances ◽  
2017 ◽  
Vol 7 (32) ◽  
pp. 20068-20075 ◽  
Author(s):  
Qiong Zhang ◽  
Rongting Guan ◽  
Xiaohe Tian ◽  
Lei Luo ◽  
Hongping Zhou ◽  
...  
Keyword(s):  
Cross Section ◽  
Living Cells ◽  
Water Soluble ◽  
Photon Absorption ◽  
Biological Applications ◽  
Two Photon Absorption ◽  
Small Water ◽  
Two Photon ◽  
Near Ir ◽  
Fluorescence Methods

Two imidazole–pyrimidine hexafluorophosphate derivatives (6P and 10P) are synthesized. The 2PA cross-section values (σ) were obtained by Z-scan and two-photon excited fluorescence methods. 6P and 10P can be used to quantify and image organelles in living cells and tissues.

Synthesis, solvatochromism and large two-photon absorption cross-sections of water-soluble dipicolinate-based pyridinium salts

2013 ◽  
Vol 99 (3) ◽  
pp. 1051-1055 ◽  
Author(s):  
Haibo Xiao ◽  
Chong Mei ◽  
Bo Li ◽  
Ning Ding ◽  
Yanzhen Zhang ◽  
...  
Keyword(s):  
Cross Sections ◽  
Water Soluble ◽  
Photon Absorption ◽  
Pyridinium Salts ◽  
Absorption Cross ◽  
Two Photon Absorption ◽  
Two Photon

Alkyl-triphenylamine end-capped triazines with AIE and large two-photon absorption cross-sections for bioimaging

2014 ◽  
Vol 2 (31) ◽  
pp. 6353-6361 ◽  
Author(s):  
Yuting Gao ◽  
Yi Qu ◽  
Tao Jiang ◽  
Hao Zhang ◽  
Nannan He ◽  
...  
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Absorption Cross Section ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Two Photon Absorption ◽  
Two Photon

Three alkyl-triphenylamine end-capped triazines (ATT-(1–3)) with AIE were synthesized, and the two-photon absorption cross section of ATT-3 was 10 003 GM.

The Medium-Depending Fluorescence of Quadrupolar Donor-Acceptor-Donor Substituted Distyrylbenzenes with High Two-Photon Absorption Cross-Sections

2006 ◽  
Vol 937 ◽  
Author(s):  
Heiner Detert ◽  
Volker Schmitt ◽  
Stefan Glang
Keyword(s):  
Cross Sections ◽  
Visible Spectrum ◽  
Solvent Polarity ◽  
Photon Absorption ◽  
Absorption Cross ◽  
Substitution Pattern ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Donor Acceptor ◽  
Emitting Species

ABSTRACT1,4-Distyrylbenzenes with terminal dialkylamino groups and a central 2,5-disubstitution with electron-accepting groups were prepared via twofold Horner-olefination. These chromophores with a quadrupolar donor-acceptor-donor substitution and C2-symmetry absorb in the violet to green region of the visible spectrum exhibit large two-photon-absorption cross-sections when irrdiated in the NIR. Whereas a variation of the solvent polarity only slightly alters the absorption spectra, the fluorescence appears to be highly responsive. Besides a positive solvatochromism, the emission is very sensitive towards protonation. Quenching or appearance of new emitting species depends on the substitution pattern and is controlled by the concentration of the acid.

scholarly journals Two-Photon Photodynamic Therapy by Water-Soluble Self-Assembled Conjugated Porphyrins

2013 ◽  
Vol 2013 ◽  
pp. 1-11 ◽  
Author(s):  
Kazuya Ogawa ◽  
Yoshiaki Kobuke
Keyword(s):  
Photodynamic Therapy ◽  
Singlet Oxygen ◽  
Cross Section ◽  
Water Soluble ◽  
Photon Absorption ◽  
Time Resolved ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Luminescence Measurement ◽  
Water Soluble Porphyrin

Studies on two-photon absorption (2PA) photodynamic therapy (PDT) by using three water-soluble porphyrin self-assemblies consisting of ethynylene-linked conjugatedbis(imidazolylporphyrin) are reviewed. 2PA cross-section values in water were obtained by an open aperture Z-scan measurement, and values were extremely large compared with those of monomeric porphyrins such as hematoporphyrin. These compounds were found to generate singlet oxygen efficiently upon one- as well as two-photon absorption as demonstrated by the time-resolved luminescence measurement at the characteristic band of singlet oxygen at 1270 nm and by using its scavenger. Photocytotoxicities for HeLa cancer cells were examined and found to be as high as those of hematoporphyrin, demonstrating that these compounds are potential candidates for 2PA-photodynamic therapy agents.

New trans-stilbene derivatives with large two-photon absorption cross-section and non-linear optical susceptibility values – a theoretical investigation

2015 ◽  
Vol 17 (18) ◽  
pp. 12299-12309 ◽  
Author(s):  
Varun Kundi ◽  
Pompozhi Protasis Thankachan
Keyword(s):  
Cross Section ◽  
Cross Sections ◽  
Photon Absorption ◽  
Active Materials ◽  
Two Photon Absorption ◽  
Two Photon ◽  
Optical Susceptibility ◽  
Trans Stilbene ◽  
Donor Acceptor ◽  
Stilbene Derivatives

In the present study, newly designed TSB derivatives decorated with suitable donor–acceptor groups have large TPA cross-sections and can be used as potential two-photon active materials.

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