Amorphous and crystalline blends from polytyrosine and pyridine-functionalized anthracene: hydrogen-bond interactions, conformations, intramolecular charge transfer and aggregation-induced emission

Shih, Ke-Ying; Lin, Yung‐Chih; Hsiao, Tai-Shen; Deng, Shiang-Lin; Kuo, Shiao‐Wei; Hong, Jin‐Long

doi:10.1039/c4py00706a

Cited by 18 publications

(14 citation statements)

References 52 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…28 Recently, they also reported that (E)-4-(2-(anthracen-9-yl)vinylpyridine (AnPy) blended with different amounts of polytyrosine through hydrogen bond interactions exhibits intramolecular charge transfer (ICT) and AIE properties at a low AnPy content. 29 Building on the studies described above, in this work, we successfully synthesized 2,6-bis(4-aminophenyl)-4-phenylpyridine (Pyridine-NH 2 ) as the initiator for the living ring-opening polymerization of L-tyrosine-N-carboxyanhydride (NCA) to obtain Pyridine-PTyr (Scheme 1). We used photoluminescence spectroscopy to investigate the fluorescence characteristics of Pyridine-NH 2 and Pyridine-PTyr.…”

Section: Introductionmentioning

confidence: 99%

Strong emission of 2,4,6-triphenylpyridine-functionalized polytyrosine and hydrogen-bonding interactions with poly(4-vinylpyridine)

Mohamed

Hong

et al. 2015

Polym. Chem.

Self Cite

View full text Add to dashboard Cite

In this paper, 2,4,6-triphenyl pyridine-functionalized polytyrosine (Pyridine-PTyr) was successfully synthesized by living ring-opening polymerization where 2,6-bis(4-aminophenyl)-4-phenylpyridine (Pyridine-NH 2 ) was an initiator. The photo-physical characteristics of Pyridine-NH 2 and Pyridine-PTyr was elucidated via UV-Vis absorption and photoluminescence spectra, revealing that unlike Pyridine-10 PTyr, Pyridine-NH 2 shows solvatochromic effects in solvents of different polarities. Additionally, Pyridine-NH 2 exhibited aggregationcaused quenching (ACQ) phenomena; however, it became an aggregation-induced emission (AIE) material after attachment to the rigidrod conformation of polytyrosine. Based on differential scanning calorimetry results, we observed that after blending Pyridine-PTyr with P4VP revealed a single glass transition temperature due to their miscibility through intermolecular hydrogen bonding of phenolic OH groups in PTyr backbone and pyridine ring in P4VP as indicated by IR spectroscopy. Obviously, the emission intensity of Pyridine-PTyr 15 was decreased after blending with P4VP and hypsochromic shift from 536 to 489 nm, presumably due to the release of the restricted intramolecular rotation of triphenyl pyridine unit in the center of the polymer and the polymer chain of Pyridine-PTyr becomes separated random coils based on WAXD results. 50 ---concluded the blending of poly(γ-benzyl-L-glutamate) (PBLG) 60 with random-coil oligomers through intermolecular hydrogen bonding to hydrogen bond donor polymers, the secondary blending with other structures of PBLG were altered. 19,20 Also, we demonstrated that the chain behavior of PTyr/P4VP blend through intermolecular hydrogen bonding in MeOH, and DMF 65 95 polypeptide through covalent chemical bonding and ionic interactions. 28 For example, Hong et al. designed two kinds of PBLG as TP1PBLG and TP2PBLG containing Scheme 1: Synthesis of (a) Pyridine-NO 2 , (b) Pyridine-NH 2 , and (c) Pyridine-PTyr tetraphenylthiophene (TP) with aggregation-induced emission property. These researchers found that the emission intensity of 5 65 Synthesis of Pyridine-PTyr by ring opening polymerization (ROP) of Tyr-NCA Tyr-NCA (3.00 g, 11.34 mmol) was weighted in a dry box under N 2 , placed in three-neck bottle, and dissolved in anhydrous DMF 70 (20 mL). The solution mixture was stirred for 15 min prior to the

show abstract

Section: Introductionmentioning

confidence: 99%

Strong emission of 2,4,6-triphenylpyridine-functionalized polytyrosine and hydrogen-bonding interactions with poly(4-vinylpyridine)

Mohamed

Hong

et al. 2015

Polym. Chem.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The synthesis of dye 1 was achieved by adapting the ligand-free Heck reaction strategy reported by Yao et al [ 25 ], where the catalyst system consisted of Pd(OAc) 2 and K 3 PO 4 in dimethylacetamide (DMA) without any triaryl phosphine ligand. On the other hand, dye 2 was synthesized following the traditional Heck reaction strategy in the presence of the ligand PPh 3 [ 22 ]. The positively charged dye 3 was simply prepared from dye 2 by refluxing in CH 3 I, followed by ion exchange in the presence of KPF 6 as described in the Experimental section.…”

Section: Resultsmentioning

confidence: 99%

“…(E)-4-(2-(Anthracen-9-yl)vinyl)pyridine ( 2 ). The synthetic route towards ( 2 ) was adopted from the strategies previously described by Shih et al [ 22 ]. To an oven-dried 50 mL Schlenk tube were added 9-bromoanthracene (1.0 g, 3.9 mmol), K 2 CO 3 (1.6 g, 11.6 mmol), PPh 3 (153 mg, 0.6 mmol) and Pd(OAc) 2 (44 mg, 0.2 mmol).…”

Section: Methodsmentioning

confidence: 99%

“…Several research groups have demonstrated the molecular stacking, crystal formation and photophysical properties of these dyes with various structural substitution [ 14 , 15 , 16 , 17 ], as well as their applications [ 18 , 19 , 20 , 21 ]. However, only a few studies have focused on the structural analogues, mono-functionalized anthracene derivatives ( Figure 1 right), and their photophysical properties [ 22 , 23 , 24 ]. Additionally, their potential use in biological systems has yet to be demonstrated.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications

et al. 2017

View full text Add to dashboard Cite

Fluorescent dyes with aggregation-induced emission (AIE) properties exhibit intensified emission upon aggregation. They are promising candidates to study biomolecules and cellular changes in aqueous environments when aggregation formation occurs. Here, we report a group of 9-position functionalized anthracene derivatives that were conveniently synthesized by the palladium-catalyzed Heck reaction. Using fluorometric analyses, these dyes were confirmed to show AIE behavior upon forming aggregates at high concentrations, in viscous solvents, and when poorly solubilized. Their photophysical properties were then further correlated with their structural features, using density functional theory (DFT) calculation. Finally, we demonstrated their potential applications in monitoring pH changes, quantifying globular proteins, as well as cell imaging with confocal microscopy.

show abstract

“…We observed that the TP unit at the center of PBLG functioned as steric blocks, due to the α-helical conformation of PBLG peptide chain, and minimized the AIE behavior. Recently, Hong et al prepared blends of 2-(anthracen-9-yl)vinylpyridine (AnPy) and PTyr, stabilized through intermolecular hydrogen bonding, that displayed intramolecular charge transfer and AIE behavior [ 43 ]. In this present study, we employed 4,4′-diamino-4″-methoxytriphenylamine (TPA-NH 2 ) as an initiator for the preparation of PTyr-TPA through ring-opening living polymerization of an l -tyrosine- N -carboxyanhydride monomer.…”

Section: Introductionmentioning

confidence: 99%

Supramolecular Interactions Induce Unexpectedly Strong Emissions from Triphenylamine-Functionalized Polytyrosine Blended with Poly(4-vinylpyridine)

2017

Self Cite

View full text Add to dashboard Cite

Abstract:In this study, we synthesized a triphenylamine-functionalized polytyrosine (PTyr-TPA) through living ring opening polymerization with 4,4 -diamino-4"-methoxytriphenylamine (TPA-NH 2 ) as an initiator, and used Fourier transform infrared (FTIR) and nuclear magnetic resonance spectroscopy to confirm the chemical structure. Photoluminescence spectroscopy revealed the photophysical properties of TPA-NH 2 and PTyr-TPA and suggested that TPA-NH 2 exhibited aggregation-caused quenching; in contrast, attaching the initiator to the rigid rod conformation of the PTyr segments caused PTyr-TPA to display aggregation-induced emission behavior. Differential scanning calorimetry revealed single glass transition temperatures for miscible PTyr-TPA/P4VP blends, the result of intermolecular hydrogen bonding between the pyridine units of P4VP and the phenolic OH units of PTyr-TPA, as confirmed through FTIR spectroscopic analyses. Furthermore, the chain behavior of PTyr-TPA transformed from a β-sheet conformation to random coils after blending with P4VP, as determined using wide-angle X-ray diffraction. These findings suggest that the decreased emission intensity of PTyr-TPA resulted from release of the restricted intramolecular rotation of the triphenylamine moiety in the polypeptide center.

show abstract

Amorphous and crystalline blends from polytyrosine and pyridine-functionalized anthracene: hydrogen-bond interactions, conformations, intramolecular charge transfer and aggregation-induced emission

Abstract: A new pyridine-terminated fluorophore of (E)-4-(2-(anthracen-9-yl)vinyl)pyridine (AnPy) with intramolecular charge transfer and aggregation-induced emission properties was synthesized and was blended with polytyrosine (PTyr) through hydrogen-bond interactions.

Cited by 18 publications

References 52 publications

Strong emission of 2,4,6-triphenylpyridine-functionalized polytyrosine and hydrogen-bonding interactions with poly(4-vinylpyridine)

Strong emission of 2,4,6-triphenylpyridine-functionalized polytyrosine and hydrogen-bonding interactions with poly(4-vinylpyridine)

9-Vinylanthracene Based Fluorogens: Synthesis, Structure-Property Relationships and Applications

Supramolecular Interactions Induce Unexpectedly Strong Emissions from Triphenylamine-Functionalized Polytyrosine Blended with Poly(4-vinylpyridine)

Contact Info

Product

Resources

About