Stereoselective Synthesis, Efficient Light Emission, and High Bipolar Charge Mobility of Chiasmatic Luminogens

Zhao, Zujin; Lam, Jacky W. Y.; Chan, Chi Ming; Chen, Shuming; Liu, Jianzhao; Lü, Ping; Rodríguez, Mario; Maldonado, José‐Luis; Ramos‐Ortíz, Gabriel; Sung, Herman H. Y.; Williams, Ian D.; Su, Huimin; Wong, Kam Sing; Ma, Yuguang; Kwok, Hoi Sing; Qiu, Huayu; Tang, Ben Zhong

doi:10.1002/adma.201102804

Cited by 109 publications

(53 citation statements)

References 32 publications

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“…[38][39][40]43,44,58 However, the highest external quantum efficiency of bilayer OLEDs utilizing them as both a light emitter and a hole transporter is 4.5% so far, 40 leaving much room for further improvement. Considering the high-lying HOMO energy levels of TPE-NB and TPE-PNPB, it is envisioned that they may also function as hole transporters in addition to light emitters in devices.…”

Section: Scheme 1 Synthetic Routes To Tpe-bridged D-a Luminogensmentioning

confidence: 98%

Rational Design of Aggregation-Induced Emission Luminogen with Weak Electron Donor–Acceptor Interaction to Achieve Highly Efficient Undoped Bilayer OLEDs

Chen

Jiang

Nie

et al. 2014

ACS Appl. Mater. Interfaces

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118

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In this work, two tailored luminogens (TPE-NB and TPE-PNPB) consisting of tetraphenylethene (TPE), diphenylamino, and dimesitylboryl as a π-conjugated linkage, electron donor, and electron acceptor, respectively, are synthesized and characterized. Their thermal stabilities, photophysical properties, solvachromism, fluorescence decays, electronic structures, electrochemical behaviors, and electroluminescence (EL) properties are investigated systematically, and the impacts of electron donor-acceptor (D-A) interaction on optoelectronic properties are discussed. Due to the presence of a TPE unit, both luminogens show aggregation-induced emission, but strong D-A interaction causes a decrease in emission efficiency and red-shifts in photoluminescence and EL emissions. The luminogen, TPE-PNPB, with a weak D-A interaction fluoresces strongly in solid film with a high fluorescence quantum yield of 94%. The trilayer OLED [ITO/NPB (60 nm)/TPE-PNPB (20 nm)/TPBi (40 nm)/LiF (1 nm)/Al (100 nm)] utilizing TPE-PNPB as a light emitter shows a peak luminance of 49 993 cd m(-2) and high EL efficiencies up to 15.7 cd A(-1), 12.9 lm W(-1), and 5.12%. The bilayer OLED [ITO/TPE-PNPB (80 nm)/TPBi (40 nm)/LiF (1 nm)/Al (100 nm)] adopting TPE-PNPB as a light emitter and hole transporter simultaneously affords even better EL efficiencies of 16.2 cd A(-1), 14.4 lm W(-1), and 5.35% in ambient air, revealing that TPE-PNPB is an eximious p-type light emitter.

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Section: Scheme 1 Synthetic Routes To Tpe-bridged D-a Luminogensmentioning

confidence: 98%

Rational Design of Aggregation-Induced Emission Luminogen with Weak Electron Donor–Acceptor Interaction to Achieve Highly Efficient Undoped Bilayer OLEDs

Chen

Jiang

Nie

et al. 2014

ACS Appl. Mater. Interfaces

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118

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“…Thee xtremely large Stokes shifts of 203 and 165 nm for f-TPE-PPy and f-TPE-PEPy further evidence their weak through-bond conjugation but efficient through-space conjugation. [22,23] Since the folded molecules are much more rigid than the linear counterparts, [25] their PL efficiencies are greatly enhanced in solutions (Table 1), owing to the suppression of intramolecular motions.…”

mentioning

confidence: 99%

Multichannel Conductance of Folded Single‐Molecule Wires Aided by Through‐Space Conjugation

Chen

Wang

et al. 2015

Angew Chem Int Ed

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Deciphering charge transport through multichannel pathways in single-molecule junctions is of high importance to construct nanoscale electronic devices and deepen insight into biological redox processes. Herein, we report two tailor-made folded single-molecule wires featuring intramolecular π-π stacking interactions. The scanning tunneling microscope (STM) based break-junction technique and theoretical calculations show that through-bond and through-space conjugations are integrated into one single-molecule wire, allowing for two simultaneous conducting channels in a single-molecule junction. These folded molecules with stable π-π stacking interaction offer conceptual advances in single-molecule multichannel conductance, and are perfect models for conductance studies in biological systems, organic thin films, and π-stacked columnar aggregates.

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“…[17,[20][21][22]24] An increasing number of examples have been reported of p-RTPl uminogens with typical through-bond conjugation;l ess attention, however,h as been paid to those with through-space conjugation, which is also effective for tuning their photophysical properties. Through-space conjugation can significantly impact the molecular conformation and charge-transfer properties of the compounds, [45,46] thus playing av ital role in the constructiono f functional materials for diverseo ptoelectronic applications, in- cluding multi-dimensional transport of carriers, organic fieldeffect transistors (OFETs), and luminescent materials. [45][46][47][48][49] Previousr eports on luminogens with through-space conjugation are mostly limited to fluorescence.…”

Section: Introductionmentioning

confidence: 99%

“…Through-space conjugation can significantly impact the molecular conformation and charge-transfer properties of the compounds, [45,46] thus playing av ital role in the constructiono f functional materials for diverseo ptoelectronic applications, in- cluding multi-dimensional transport of carriers, organic fieldeffect transistors (OFETs), and luminescent materials. [45][46][47][48][49] Previousr eports on luminogens with through-space conjugation are mostly limited to fluorescence. [46,48,49] Only af ew scattered examples of nonconventional luminogens with al ack of remarkable conjugates have dealt with (p-)RTP emissions.…”

Section: Introductionmentioning

confidence: 99%

“…[45][46][47][48][49] Previousr eports on luminogens with through-space conjugation are mostly limited to fluorescence. [46,48,49] Only af ew scattered examples of nonconventional luminogens with al ack of remarkable conjugates have dealt with (p-)RTP emissions. [18,[50][51][52] In this contribution, we therefore investigated the Diels-Alder cycloaddition adduct of anthracene (AN) and maleic anhydride (MA), or AN-MA, which consists of two phenylg roups rich in p electrons and an anhydride moiety with abundant lone pairs (n)( Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

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Polymorphic Pure Organic Luminogens with Through‐Space Conjugation and Persistent Room‐Temperature Phosphorescence

Zhang

Zhao

et al. 2019

Chemistry An Asian Journal

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Pure organic luminogens with persistent room‐temperature phosphorescence (p‐RTP) have attracted increasing attention owing to their vital significance and potential applications in security inks, bioimaging, and photodynamic therapy. Previously reported p‐RTP luminogens normally possessed through‐bond conjugation. In this work, we report a pure organic luminogen, AN‐MA, the Diels–Alder cycloaddition adduct of anthracene (AN) and maleic anhydride (MA), which possesses isolated phenyl groups and an anhydride moiety. AN‐MA exhibits aggregation‐enhanced emission (AEE) characteristics with efficiency of approximately 2 % and up to 8.5 % in solution and crystals, respectively. Two polymorphs of AN‐MA were readily obtained that were able to generate UV emission from individual phenyl rings together with bright blue emission owing to the effective through‐space conjugation. Moreover, p‐RTP with a lifetime of up to approximately 1.6 s was obtained in the crystals. These results not only reveal a new system with both fluorescence and RTP dual emission but also suggest an alternative through‐space conjugation strategy towards pure organic p‐RTP luminogens with tunable emissions.

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Stereoselective Synthesis, Efficient Light Emission, and High Bipolar Charge Mobility of Chiasmatic Luminogens

Cited by 109 publications

References 32 publications

Rational Design of Aggregation-Induced Emission Luminogen with Weak Electron Donor–Acceptor Interaction to Achieve Highly Efficient Undoped Bilayer OLEDs

Rational Design of Aggregation-Induced Emission Luminogen with Weak Electron Donor–Acceptor Interaction to Achieve Highly Efficient Undoped Bilayer OLEDs

Multichannel Conductance of Folded Single‐Molecule Wires Aided by Through‐Space Conjugation

Polymorphic Pure Organic Luminogens with Through‐Space Conjugation and Persistent Room‐Temperature Phosphorescence

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