Electrochemical and optoelectronic properties of terthiophene- and bithiophene-based polybenzofulvene derivatives

Biani, Fabrizia Fabrizi de; Reale, Annalisa; Razzano, Vincenzo; Paolino, Marco; Giuliani, Germano; Donati, Alessandro; Giorgi, Gianluca; Mróz, Wojciech; Piovani, Daniele; Botta, Chiara; Cappelli, Andrea

doi:10.1039/c7ra13242e

Cited by 15 publications

(8 citation statements)

References 37 publications

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“…In particular, interesting new drug delivery systems were developed through the insertion of oligoethylene glycol (OEG) side chain or the conjugation with biocompatible macromolecules [33,34,35,36,37,38,39,40]. Moreover, the structural manipulation of the 3-phenylindene moiety has provided intriguing results in the optoelectronic field, leading to potentially useful polymers in the fabrication of OLED devices [41,42,43,44,45,46,47,48]. However, these results were obtained after intensive structure-property relationship studies were performed on monomer BF1 and focused on the identification of the effects of different substituents on the polymer properties (i.e., spontaneous polymerization, molecular weight distribution, structure, thermoreversibility, photophysical features, and aggregation).…”

Section: Introductionmentioning

confidence: 99%

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

et al. 2018

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Spontaneous polymerization is an intriguing phenomenon in which pure monomers begin their polymerization without initiators or catalysts. Previously, 3-phenylbenzofulvene monomers were found to polymerize spontaneously after solvent removal. Here, eight new 3-substituted benzofulvene monomers 1a-h were synthesized in order to investigate the effects of differently substituted aromatic rings in position 3 of the benzofulvene scaffold on spontaneous polymerization. The newly synthesized monomers maintained the tendency toward spontaneous polymerization. However, monomer 1a, bearing an ortho-methoxy substituted phenyl, polymerized hardly, thus producing low polymerization yields, inhomogeneous structure, and low molecular weight of the obtained polymeric material. This result suggested the importance of the presence of hydrogen atoms in the 2 -position to achieve productive interactions among the monomers in the recognition step preluding the spontaneous polymerization and among the monomeric units in the polybenzofulvene backbones. Moreover, this study paves the way to modify the pendant rings in position 3 of the indene scaffold to synthesize new polybenzofulvene derivatives variously decorated.

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Section: Introductionmentioning

confidence: 99%

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

et al. 2018

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“…More specifically, 1 features an extended conjugation due to a 3phenylindene-2-carboxylate scaffold, the structure at the basis of the polybenzofulvene monomeric unit (Figure 1C). [52][53][54][55][56][57][58][59][60][61][62][63][64][65] We also show that the obtained LDMS 1 can be easily functionalized with a clickable azide group (compound 2) for the insertion of the photoswitch in more complex synthetic and/or biological structures via azide-alkyne click reactions. In fact, we report that methyl-end-capped nona(ethylene glycol) (NEG) side chain, an amphiphilic solubilizing group, [66] can be successfully conjugated with 2 in a preliminary effort to obtain an amphiphilic LDMS capable of self-assembling in nanometric micelles in water solution and operated by visible light (Figure 1D).…”

Section: Introductionmentioning

confidence: 70%

Design, Synthesis and Characterization of a Visible‐Light‐Sensitive Molecular Switch and Its PEGylation Towards a Self‐Assembling Molecule

Paolino

Reale

Licciardi

et al. 2022

Chemistry A European J

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HBDI‐like chromophores represent a novel set of biomimetic switches mimicking the fluorophore of the green fluorescent protein that are currently studied with the hope to expand the molecular switch/motor toolbox. However, until now members capable of absorbing visible light in their neutral (i. e. non‐anionic) form have not been reported. In this contribution we report the preparation of an HBDI‐like chromophore based on a 3‐phenylbenzofulvene scaffold capable of absorbing blue light and photoisomerizing on the picosecond timescale. More specifically, we show that double‐bond photoisomerization occurs in both the E‐to‐Z and Z‐to‐E directions and that these can be controlled by irradiating with blue and UV light, respectively. Finally, as a preliminary applicative result, we report the incorporation of the chromophore in an amphiphilic molecule and demonstrate the formation of a visible‐light‐sensitive nanoaggregated state in water.

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“…In general, PPBFB derivatives are amphiphilic macromolecules capable of interacting with a wide range of solvents. In particular, previously published poly-6-MOEG-9-TM- BF3k (obtained by means of the “grafting through” or “grafting onto” approaches) showed an excellent solubility in the most common organic solvents [22,23]. Its dissolution in dichloromethane or chloroform is very rapid, while the interaction with water is slower, but it led, however, to transparent solutions.…”

Section: Resultsmentioning

confidence: 99%

“…The characterization studies suggested, for this hydrophobic polybenzofulvene derivative, a vinyl structure stabilized by aromatic stacking interactions [9,10]. This intriguing finding led us to explore the chemistry of benzofulvene derivatives [11,12,13,14,15], and to prepare intriguing materials with potential applications in the optoelectronic field [16,17,18,19,20,21,22,23] and pharmaceutical science [24].…”

Section: Introductionmentioning

confidence: 99%

Densely PEGylated Polybenzofulvene Brushes for Potential Applications in Drug Encapsulation

et al. 2018

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The technique of grafting side chains onto a linear polymeric backbone is commonly used to confer to the new polymeric material with desired properties, such as tunable solubility, ionic charge, biocompatibility, or specific interactions with biological systems. In this paper, two new polybenzofulvene backbones were assembled by spontaneous polymerization of the appropriate benzofulvene monomers (4,6-PO-BF3k and 4’,6-PO-BF3k) bearing two clickable propargyloxy groups in different positions of the 3-phenylindene scaffold. Poly-4,6-PO-BF3k and poly-4’,6-PO-BF3k were grafted with monomethyl oligo(ethylene glycol) (MOEG) to prepare two new polybenzofulvene brushes (i.e., poly-4,6-MOEG-9-TM-BF3k and poly-4’,6-MOEG-9-TM-BF3k) by means of a “grafting onto” approach, that were characterized from the point of view of their macromolecular features, aggregation liability, and in a preliminary evaluation of biocompatibility. The obtained results make these PEGylated polybenzofulvene brushes (PPBFB) derivatives potentially useful as nanocarriers for nanoencapsulation and delivery of drug molecules.

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Electrochemical and optoelectronic properties of terthiophene- and bithiophene-based polybenzofulvene derivatives

Abstract: The electrochemical behavior of some polybenzofulvene derivatives bearing bithiophene (BT) or terthiophene (TT) side chains was investigated by cyclic voltammetry and cross-linked materials were obtained by dimerization of the BT or TT side chains.

Cited by 15 publications

References 37 publications

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

Structural Manipulation of the Conjugated Phenyl Moiety in 3-Phenylbenzofulvene Monomers: Effects on Spontaneous Polymerization

Design, Synthesis and Characterization of a Visible‐Light‐Sensitive Molecular Switch and Its PEGylation Towards a Self‐Assembling Molecule

Densely PEGylated Polybenzofulvene Brushes for Potential Applications in Drug Encapsulation

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