Locked Planarity: A Strategy for Tailoring Ladder-Type π-Conjugated Anilido–Pyridine Boron Difluorides

Hao, Qingshan; Yu, Shuai; Li, Shayu; Chen, Jinping; Zeng, Yi; Yu, Tianjun; Yang, Guoqiang; Li, Yang

doi:10.1021/jo402583y

Cited by 25 publications

(27 citation statements)

References 49 publications

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“…The lack of any double borylation with a range of boron electrophiles is attributed to the initial borylation reducing the nucleophilicity of the other nitrogen atom in benzothiadiazole preventing coordination of a second boron Lewis acid. 18 …”

Section: Resultsmentioning

confidence: 99%

Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

et al. 2015

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Section: Resultsmentioning

confidence: 99%

Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

et al. 2015

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“…Taking the typical dye boron dipyrromethene (BODIPY) as an example, the precursor 64 , usually synthesized from pyrrole derivatives and aldehydes, is readily to obtain the BODIPY skeleton 65 by adding BF 3 •OEt 2 /Et 3 N (Loudet and Burgess, 2007 ). This reaction condition is widely applicable to the precursors with the features of containing amino group and aromatic nitrogen atoms at appropriate positions, e.g., 66 , 67 , 68 , and 69 (Araneda et al, 2011 ; Nawn et al, 2013 ; Hao et al, 2014 ; Qiu et al, 2016 ).…”

Section: Synthesis Routesmentioning

confidence: 99%

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

Huang

2018

Front. Chem.

109

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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.

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“…Existing strategies to lower the symmetry of the parent dipyrromethene ligand system (Figure ) involve: 1) replacing the amido N‐donor with anionic imidazolate, indolate, carbazolate, anilide, O‐donor, or C‐donor units; 2) replacing the imino N‐donor with charge‐neutral pyridine, quinoline, pyrimidine, thiazole, or imine groups.…”

Section: Introductionmentioning

confidence: 97%

BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

Lee

Park

Cho

et al. 2016

Chemistry A European J

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A series of air-stable boron complexes 1-5 were prepared by using N-aryl iminopyrrolide ligands. Designed as minimalist structural mimics of the privileged BODIPY motif, these new BOIMPY (BOron complexes of IMinoPYrrolide ligands) fluorophores feature low molecular symmetry that promotes emission from CT-type excited states with large Stokes shifts and little self-quenching. Through comparative studies on the homologous set of compounds 1-4, we have confirmed that a delicate interplay between conformational twisting and donor-acceptor interaction dictates the mechanism of de-excitation, which responds sensitively to solvent polarity as well as protonation states. Over a wide visible spectral range, the structure-dependent light-emitting properties of BOIMPY molecules are well manifested, even in the solid-state. In order to exploit the environment-sensitive nature of CT-type emission, the BOIMPY motif was elaborated further into a bioprobe molecule 5. Live-cell fluorescence imaging studies have established that 5 is localized exclusively at lipid droplets to produce well-resolved staining patterns without affecting cell viability. These findings promise future elaboration of BOIMPY-based functional molecules for applications in biological imaging, chemical sensing, and molecular switching.

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Locked Planarity: A Strategy for Tailoring Ladder-Type π-Conjugated Anilido–Pyridine Boron Difluorides

Cited by 25 publications

References 49 publications

Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

Enhancing electron affinity and tuning band gap in donor–acceptor organic semiconductors by benzothiadiazole directed C–H borylation

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

BOIMPY: Fluorescent Boron Complexes with Tunable and Environment‐Responsive Light‐Emitting Properties

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