Giant Domain Formation in a Thin Film of Bisstyrylanthracene Derivatives by a Simple Melt Process

Konishi, Misuzu; Fujita, Katsuhiko; Tsutsui, Tetsuo

doi:10.1080/15421400490506432

Cited by 6 publications

(7 citation statements)

References 9 publications

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“…Simply, 4-(hexadecyloxy)benzaldehyde, BODIPY 1, and BODIPY 2 were prepared according to the literature methods with slight modification. 63,64 palladium (Pd(PPh 3 ) 4 ), copper iodide (CuI) and diisopropylamine. After purification, the products were acquired and characterized by proton nuclear magnetic resonance ( 1 H NMR) and matrix-assisted laser desorption/ionization time-offlight mass spectrometry.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The synthetic routes of C16 pBDP are demonstrated in Scheme . Simply, 4-(hexadecyloxy)benzaldehyde, BODIPY 1 , and BODIPY 2 were prepared according to the literature methods with slight modification. , BODIPY 3 was prepared by the Sonogashira reaction of BODIPY 2 with ethynyltrimethylsilane. Subsequently, BODIPY 4 was obtained by hydrolysis of 2,6-ethynyltrimethylsilane substituted monomer BODIPY 3 under the existence of tetrabutylammonium fluoride.…”

Section: Resultsmentioning

confidence: 99%

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Hybrid Nanomaterials of Conjugated Polymers and Albumin for Precise Photothermal Therapy

Zhang

Lin

Wang

et al. 2018

ACS Appl. Mater. Interfaces

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Heretofore, conjugated polymers (CPs) attract considerable attention in photothermal therapy (PTT). Although various CPs with different structures have been reported, the suboptimal circulation persistence and biodistribution limit their efficacy in tumor treatment. Human serum albumin (HSA), an endogenous plasma protein, has been widely functioned as a carrier for therapeutic agents. Herein, we construct nanocomplex C16 pBDP@HSA nanoparticles (NPs) from hydrophobic 4,4-difluoro-4-bora-3a,4adiaza-s-indacene (BODIPY)-containing CPs and HSA, which exhibit robust stability in physiological conditions and excellent photothermal activity upon irradiation. The high photothermal conversion efficiency of 37.5%, higher than that of other reported PTT agents such as gold nanorods, phosphorus quantum dots, and 2D materials, results in the potent photocytotoxicity toward cancer cells. Simultaneously, C16 pBDP@HSA NPs' capabilities of near-infrared fluorescence and photoacoustic imaging can provide guidance to the PTT. The outstanding inhibition of tumor growth results from great photothermal activity, the benefited accumulation in tumor, and optimal timing of treatment. To the best of our knowledge, this is the first study which combines the BODIPY-based CPs and HSA in one nanostructure and finds application in cancer treatment. Moreover, this article also offers a new strategy for other insoluble macromolecules to explore more biomedical applications.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Hybrid Nanomaterials of Conjugated Polymers and Albumin for Precise Photothermal Therapy

Zhang

Lin

Wang

et al. 2018

ACS Appl. Mater. Interfaces

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“…1) with long alkyl chains of varing length, BSAn (n ¼ 10, 12, 13, 14, 15, 16, 18, 20), were synthesized as described elsewhere. 8) Differential scanning calorimetry (DSC) was carried out using DSAQ100 (TA Instruments) at the rate of 0.5 C/min. Each BSA derivative (5 mg) was sealed in an Al pan.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…The large monodomain films were prepared by the meltfreezing process. 8) Several mg of a BSA derivative were placed in between two cleaned glass plates. After heating at 140 C the melt was spread over the gap by capillary action.…”

Section: Experimental Methodsmentioning

confidence: 99%

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Large Domain Film of Bis(styrilanthracene) Derivatives Prepared by a Simple Melt-Freezing Process and the Improvement of Field Effect Hole Mobility

Konishi¹,

Fujita

Tsutsui

2008

jjap

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Bis(styrylanthracene) (BSA) derivatives with long alkyl side chains form thin films consisting of large domains (mm-scale) at room temperature by a simple melt-freezing process. It is revealed by X-ray diffraction that the homogeneous domains are in a single-crystal-like solid state. The film assumes a layered structure withstacking parallel to the film plane. The hole mobility of the field effect transistor composed of the monodomain film is almost two orders of magnitude higher than that of the corresponding amorphous film. This result may be due tostacking developed in the carrier transport direction.

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Synthesis, Properties, and Solar Cell Performance of Poly(4‐(p‐alkoxystyryl)thiazole)s

Jäger

Schraff

Pammer

2018

Macro Chemistry & Physics

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A series of polythiazoles (PvTzs) featuring conjugated styryl sidechains equipped with different solubilizing p‐alkoxy‐groups (OR, R = n‐octyl, n‐dodecyl, 2‐ethylhexyl, 2‐hexyldecyl) is prepared by Negishi‐coupling polycondensation. Soluble material with number‐average molecular weights of up to Mn = 8.5 kDa (polydispersity (PDI) = 1.3, degree of polymerization (DPn) ≈ 20) is obtained, with a head‐to‐tail content of the PvTzs of ≈77%, as estimated from comparison with reference polymers. The polymers exhibit optical absorption properties similar to their polythiophene analogues, while their electrochemical characterization shows a significant stabilization of their frontier orbital levels. Fluorescence measurements indicate that upon excitation of the electron rich alkoxystyryl side‐chains charge transfer onto the more electron deficient polythiazole backbone occurs. This finding is corroborated by density functional theory (DFT) calculations on oligomeric model systems, which also consistently reproduce the optical properties observed for the polymers. The potentialities of these materials for applications in organic electronics can be demonstrated by their use as donor materials in organic photovoltaic cells, which exhibit higher open circuit voltages (VOC, up to 0.86 V) than P3HT‐ or analogous polythiophene‐based cells (VOC = 0.5–0.6 V).

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Giant Domain Formation in a Thin Film of Bisstyrylanthracene Derivatives by a Simple Melt Process

Cited by 6 publications

References 9 publications

Hybrid Nanomaterials of Conjugated Polymers and Albumin for Precise Photothermal Therapy

Hybrid Nanomaterials of Conjugated Polymers and Albumin for Precise Photothermal Therapy

Large Domain Film of Bis(styrilanthracene) Derivatives Prepared by a Simple Melt-Freezing Process and the Improvement of Field Effect Hole Mobility

Synthesis, Properties, and Solar Cell Performance of Poly(4‐(p‐alkoxystyryl)thiazole)s

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