Geometric and Electronic Structures of Boron(III)‐Cored Dyes Tailored by Incorporation of Heteroatoms into Ligands

Sun, Lin; Zhang, Fan; Wang, Xinyang; Qiu, Feng; Xue, Minzhao; Tregnago, Giulia; Cacialli, Franco; Osella, Silvio; Beljonne, David; Feng, Xinliang

doi:10.1002/asia.201403272

Cited by 15 publications

(5 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The low fluorescence quantum yield of OBN-DHPP in CH 2 Cl 2 , determined using an integrating sphere, is probably due to the low-rigidity molecular skeleton and rotatable phenyl substituents. 22,23 Moreover, the UV−vis absorption and PL spectra of OBN-DHPP-PEG 45 in CH 2 Cl 2 show little differ- Longest absorption maximum. b Emission maximum upon excitation at the longest absorption maximum.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Relative to its absorption spectrum, OBN-DHPP has a broad emission profile with a large Stokes shift of 64935.1 cm –1 , which is caused by its low-rigidity backbone. The low fluorescence quantum yield of OBN-DHPP in CH 2 Cl 2 , determined using an integrating sphere, is probably due to the low-rigidity molecular skeleton and rotatable phenyl substituents. , Moreover, the UV–vis absorption and PL spectra of OBN-DHPP-PEG 45 in CH 2 Cl 2 show little differences compared with those of OBN-DHPP , indicative of the weak influence of PEG on the conjugated backbone of OBN-DHPP . The photophysical properties of OBN-DHPP and OBN-DHPP-PEG 45 are summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

et al. 2018

Self Cite

View full text Add to dashboard Cite

Multifunction luminogens have emerged as promising candidates in high-performance sensor and imaging systems. Concise approaches to the synthesis of such molecules are urgently required both for fundamental research and technological applications. In this study, a new symmetric ligand of di(2-hydroxyphenyl)phthalazine with multiple binding sites around a phthalazine unit was readily synthesized, which could be converted efficiently into an asymmetric luminogen (OBN-DHPP) through the formation of oxygen−boron−nitrogen bonding. This molecule has a twistable π-extended backbone with a tetracoordinated boron core bearing two bulky phenyl groups, giving it abundant optical properties including a large Stokes shift piezochromism and aggregationinduced emission enhancement. Importantly, the presence of a free phenolic hydroxyl group in the backbone of OBN-DHPP enables the incorporation of various functional moieties into the asymmetric luminogen. As an example, polyethylene glycol (PEG)-modified luminogen (OBN-DHPP-PEG 45 ) was synthesized. In the aqueous medium, OBN-DHPP-PEG 45 could self-assemble into spherical nanoparticles with low cytotoxicity and excellent emission performance as well as high solubility. The results of flow cytometry and fluorescence microscopy reveal that these nanoparticles could be internalized successfully by HeLa cells, demonstrating their potential application in bioimaging.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

et al. 2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…In contrast, the introduction of four-coordinate boron units into various sp 2 -carbon skeletons leads to the synthesis of boron-containing chromophores, which have achieved significant progress. [127][128][129][130][131] In this Account, both the weak B,N-coordinated bond and the strong B,N-covalent bond are considered NBN systems. Interestingly, this four-coordinate NBN system not only possesses a shapepersistent molecular skeleton but also has a great influence on controlling molecular packing and optical and electronic properties.…”

Section: Account Syn Lettmentioning

confidence: 99%

Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

Liu

Feng

2019

Synlett

Self Cite

View full text Add to dashboard Cite

Bottom-up organic synthesis serves as an efficient method to provide atomically precise heteroatom-doped polycyclic aromatic hydrocarbons (PAHs) with not only well-defined size and edge structures but also specific concentrations and positions of the heteroatoms. We provide a plenary account of the preparation of nitrogen-doped PAHs (N-PAHs) through 1,3-dipolar cycloaddition between different dipolarophiles, as well as pyrazine-type N-doped diaza-hexa-peri-hexabenzocoronene (diaza-HBC). Additionally, we present the synthesis of a class of helical N-charged PAHs, including one charged aza[5]helicene and two charged aza[4]helicenes. Moreover, the bottom-up organic synthesis strategy is further extended to the construction of novel nitrogen-boron-nitrogen (NBN)-containing PAHs. Finally, we discuss the synthesis of four-coordinate boron chromophores containing 6,12,18-tris(alkyl amine)-5,11,17-triazatrinaphthylene derivative ligands.1 Introduction2 Nitrogen-Doped PAHs Based on Dibenzo-9a-azaphenalene (DBAP)3 Cationic Nitrogen-Doped Helical PAHs4 Nitrogen–Boron–Nitrogen-Doped PAHs5 Conclusion and Outlook

show abstract

“…A family of conjugated molecules containing N–B←N groups has been intensively explored as fluorescence dyes with high absorption coefficients and fluorescence quantum efficiency, which were widely utilized in OSCs, OLEDs, sensing, and imaging, etc (Li et al, 2013 ; Fu et al, 2015 ; Lin et al, 2015 ; Dou et al, 2017 ). The synthesis routes toward N–B←N groups usually require a precursor equipped with an amino group and an aromatic nitrogen at suitable position for chelation of the boron.…”

Section: Synthesis Routesmentioning

confidence: 99%

BN Embedded Polycyclic π-Conjugated Systems: Synthesis, Optoelectronic Properties, and Photovoltaic Applications

Huang

2018

Front. Chem.

114

View full text Add to dashboard Cite

In the periodic table of elements, boron (B, atomic number, 5) and nitrogen (N, atomic number, 7) are neighboring to the carbon (C, atomic number, 6). Thus, the total electronic number of two carbons (12) is equal to the electronic sum of one boron (5) and one nitrogen (7). Accordingly, replacing two carbons with one boron and one nitrogen in a π-conjugated structure gives an isoelectronic system, i.e., the BN perturbed π-conjugated system, comparing to their all-carbon analogs. The BN embedded π-conjugated systems have unique properties, e.g., optical absorption, emission, energy levels, bandgaps, and packing order in contrast to their all-carbon analogs and have been intensively studied in terms of novel synthesis, photophysical characterizations, and electronic applications in recent years. In this review, we try to summarize the synthesis methods, optoelectronic properties, and progress in organic photovoltaic (OPV) applications of the representative BN embedded polycyclic π-conjugated systems. Firstly, the narrative will be commenced with a general introduction to the BN units, i.e., B←N coordination bond, B-N covalent bond, and N-B←N group. Then, the representative synthesis strategies toward π-conjugated systems containing B←N coordination bond, B-N covalent bond, and N-B←N group will be summarized. Afterwards, the frontier orbital energy levels, optical absorption, packing order in solid state, charge transportation ability, and photovoltaic performances of typical BN embedded π-conjugated systems will be discussed. Finally, a prospect will be proposed on the OPV materials of BN doped π-conjugated systems, especially their potential applications to the small molecules organic solar cells.

show abstract

Geometric and Electronic Structures of Boron(III)‐Cored Dyes Tailored by Incorporation of Heteroatoms into Ligands

Cited by 15 publications

References 44 publications

Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

Asymmetric Boron-Cored Aggregation-Induced Emission Luminogen with Multiple Functions Synthesized through Stepwise Conversion from a Symmetric Ligand

Bottom-Up Synthesis of Nitrogen-Doped Polycyclic Aromatic Hydrocarbons

BN Embedded Polycyclic π-Conjugated Systems: Synthesis, Optoelectronic Properties, and Photovoltaic Applications

Contact Info

Product

Resources

About