Novel silicon naphthalocyanines: synthesis and molecular arrangement in thin films

Katayose, Mitsuo; Tai, Seiji; Kamijima, Kouichi; Hagiwara, Hideo; Hayashi, Naoaki

doi:10.1039/p29920000403

Cited by 32 publications

(29 citation statements)

References 7 publications

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“…Larger red-shifts correlate with a decrease in the center-to-center distance in a J-aggregate type structure. 27,28 Therefore, the increased red-shift observed after annealing is consistent with the improved transport properties Langmuir Article dx.doi.org/10.1021/la204486y | Langmuir 2012, 28, 6192−6200 due to enhanced π−π overlap between adjacent OBNc molecules in a J-aggregate structure. Even though the interplanar spacing of OBNc exceeds that in vacuum-deposited H 2 Pc, the field-effect mobilities obtained are superior for the naphthalocyanines.…”

Section: ■ Results and Discussionsupporting

confidence: 75%

Air-Stable Spin-Coated Naphthalocyanine Transistors for Enhanced Chemical Vapor Detection

et al. 2012

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Air-stable organic thin-film transistor (OTFT) sensors fabricated using spin-cast films of 5,9,14,18,23,27,32,36-octabutoxy-2,3-naphthalocyanine (OBNc) demonstrated improved chemical vapor sensitivity and selectivity relative to vacuum-deposited phthalocyanine (H(2)Pc) OTFTs. UV-vis spectroscopy data show that annealed spin-cast OBNc films exhibit a red-shift in the OBNc Q-band λ(max) which is generally diagnostic of improved π-orbital overlap in phthalocyanine ring systems. Annealed OBNc OTFTs have mobilities of 0.06 cm(2) V(-1) s(-1), low threshold voltages (|V(th)| < 1 V), and on/off ratios greater than 10(6). These air-stable device parameters are utilized for sensing modalities which enhance the sensitivity and selectivity of OBNc OTFTs relative to H(2)Pc OTFTs. While both sensors exhibit mobility decreases for all analytes, only OBNc OTFTs exhibit V(th) changes for highly polar/nonpolar analytes. The observed mobility decreases for both sensors are consistent with electron donation trends via hydrogen bonding by basic analytes. In contrast, V(th) changes for OBNc sensors appear to correlate with the analyte's octanol-water partition coefficient, consistent with polar molecules stabilizing charge in the organic semiconductor film. The analyte induced V(th) changes for OBNc OTFTs can be employed to develop selective multiparameter sensors which can sense analyte stabilized fixed charge in the film.

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Section: ■ Results and Discussionsupporting

confidence: 75%

Air-Stable Spin-Coated Naphthalocyanine Transistors for Enhanced Chemical Vapor Detection

et al. 2012

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“…Reacting 1,3-diiminopyrrolino(3,4-c)pyridine with tetrachlorosilane gave the dichlorosilicon-tetrapyridinoporphyrazine which was then quantitatively hydrolyzed to afford the dihydroxysilicon-TPyPz. The bis(trihexylsiloxy)silicon-tetrapyridinoporphyrazine 1 was then formed through a conventional silylating method used for phthalocyanines (27)(28)(29). Thus, the dihydroxy derivative was reacted with trihexylchlorosilane in refluxing pyridine to afford 1 in better yields than those reported in a patent for the preparation of related compounds (30).…”

Section: Synthesismentioning

confidence: 99%

Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

Martí¹,

Nonell²,

Nicolau³

et al. 2000

Photochemistry and Photobiology

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We describe the synthesis and photophysical properties of a series of neutral and cationic 3,4-tetrapyridinoporphyrazines, potential lead photosensitizers for photodynamic inactivation of bacteria. Tetracationic TPyPzs exist essentially as monomers in aqueous systems, but the presence of trialkylated compounds due to incomplete quaternization of the outer nitrogen atoms induces severe aggregation. The absorption, fluorescence, triplet, and singlet oxygen quantum yields for both the neutral and cationic compounds are comparable to those of the related phthalocyanines.

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“…Furthermore, the absorbance maximum of activatable nanoparticles loaded with the highest amount of SiNc (6% SiNc/polymer) was red shifted by 10 nm from the Q-band maximum of monomeric SiNc (Figure S1 ). Katayose et al previously revealed that packed SiNc molecules with axial substituents exhibit a red shift of Q-band absorption and the red-shift value is mainly dependent on the center-to-center distance between molecules 40 . It was also demonstrated that the red-shift value increases with a decrease in the distance between SiNc molecules.…”

Section: Resultsmentioning

confidence: 99%

A Tumor-Activatable Theranostic Nanomedicine Platform for NIR Fluorescence-Guided Surgery and Combinatorial Phototherapy

et al. 2018

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Fluorescence image-guided surgery combined with intraoperative therapeutic modalities has great potential for intraoperative detection of oncologic targets and eradication of unresectable cancer residues. Therefore, we have developed an activatable theranostic nanoplatform that can be used concurrently for two purposes: (1) tumor delineation with real-time near infrared (NIR) fluorescence signal during surgery, and (2) intraoperative targeted treatment to further eliminate unresected disease sites by non-toxic phototherapy.Methods: The developed nanoplatform is based on a single agent, silicon naphthalocyanine (SiNc), encapsulated in biodegradable PEG-PCL (poly (ethylene glycol)-b-poly(ɛ-caprolactone)) nanoparticles. It is engineered to be non-fluorescent initially via dense SiNc packing within the nanoparticle's hydrophobic core, with NIR fluorescence activation after accumulation at the tumor site. The activatable nanoplatform was evaluated in vitro and in two different murine cancer models, including an ovarian intraperitoneal metastasis-mimicking model. Furthermore, fluorescence image-guided surgery mediated by this nanoplatform was performed on the employed animal models using a Fluobeam® 800 imaging system. Finally, the phototherapeutic efficacy of the developed nanoplatform was demonstrated in vivo.Results: Our in vitro data suggest that the intracellular environment of cancer cells is capable of compromising the integrity of self-assembled nanoparticles and thus causes disruption of the tight dye packing inside the hydrophobic cores and activation of the NIR fluorescence. Animal studies demonstrated accumulation of activatable nanoparticles at the tumor site following systemic administration, as well as release and fluorescence recovery of SiNc from the polymeric carrier. It was also validated that the developed nanoparticles are compatible with the intraoperative imaging system Fluobeam® 800, and nanoparticle-mediated image-guided surgery provides successful resection of cancer tumors. Finally, in vivo studies revealed that combinatorial phototherapy mediated by the nanoparticles could efficiently eradicate chemoresistant ovarian cancer tumors.Conclusion: The revealed properties of the activatable nanoplatform make it highly promising for further application in clinical image-guided surgery and combined phototherapy, facilitating a potential translation to clinical studies.

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Novel silicon naphthalocyanines: synthesis and molecular arrangement in thin films

Cited by 32 publications

References 7 publications

Air-Stable Spin-Coated Naphthalocyanine Transistors for Enhanced Chemical Vapor Detection

Air-Stable Spin-Coated Naphthalocyanine Transistors for Enhanced Chemical Vapor Detection

Photophysical Properties of Neutral and Cationic Tetrapyridinoporphyrazines

A Tumor-Activatable Theranostic Nanomedicine Platform for NIR Fluorescence-Guided Surgery and Combinatorial Phototherapy

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