Triphenylamine-equipped 1,8-naphthaolactam: a versatile scaffold for the custom design of efficient subcellular imaging agents

Li, Yingzhong; Chen, Lizhen; Si, Leilei; Yang, Yang; Zhou, Chunlei; Yu, Fu-Qing; Xia, Guomin; Wang, Hongming

doi:10.1039/d2tb02528k

Cited by 3 publications

(2 citation statements)

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“…The obtained results are presented in Table . All the compounds showed the more significant Stokes shift, signifying the geometrical change between the ground and excited state, and that benefits the CT among the donor and acceptor moieties. , …”

Section: Resultsmentioning

confidence: 97%

“…All the compounds showed the more significant Stokes shift, signifying the geometrical change between the ground and excited state, and that benefits the CT among the donor and acceptor moieties. 37,38 Electrochemical Behavior. The electrochemical characteristics of compounds 7a−e were analyzed by cyclic voltammetry, and the cyclic voltammograms are displayed in Figure S22, and the results are consolidated in Table 2.…”

Section: Nmr Ft-ir and Hr-ms Techniques (Figures S1−s20)mentioning

confidence: 99%

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Exploring the Transformation of Static Random Access Memory to Write-Once-Read-Many-Times Memory Behavior in Imidazole–Triphenylamine-Based Devices

Harshini,

Angela,

Imran

et al. 2024

ACS Appl. Electron. Mater.

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A series of D−A, A−D−D, and A−D−A-based compounds with imidazole and triphenylamine were designed and synthesized to study the memristor performance. The D−A system was functionalized with different substitutions (phenyl, anthracene, and indoloquinoxaline) in the terminal position of triarylamine to alter the coplanarity and conjugation length. The electrochemical investigations showed an irreversible anodic peak (1.01−1.25 V) with a band gap of 2.72−3.05 eV, and the photophysical studies revealed the intramolecular charge transfer. The compound with simple imidazole and triphenylamine exhibited static random access memory (SRAM) behavior due to the coplanar structure back charge transfer (CT). Besides, the A−D−D-based system with an anthracene substituent displayed the binary write-once-read-many-times (WORM) memory with the ON/OFF current ratio of 10 4 . The indoloquinoxaline-substituted compound notably showed a ternary WORM memory due to two different charge-trapping centers in the A− D−A system. The devices with end-capped triphenylamine exhibited a long-lasting retention time (2 × 10 3 ) and endurance cycles. The molecular simulations unveiled the underlying mechanism for the conversion from SRAM to WORM via altering the dihedral angle by different substituents. Moreover, the compounds CT and charge trap support the binary and ternary WORM-based memory devices. This work demonstrates the strategy to convert the SRAM into WORM memory behavior by preventing the back CT from an excited state to the ground state.

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Section: Resultsmentioning

confidence: 97%

Section: Nmr Ft-ir and Hr-ms Techniques (Figures S1−s20)mentioning

confidence: 99%

Exploring the Transformation of Static Random Access Memory to Write-Once-Read-Many-Times Memory Behavior in Imidazole–Triphenylamine-Based Devices

Harshini,

Angela,

Imran

et al. 2024

ACS Appl. Electron. Mater.

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Stable peri‐Naphthoisatogens without C2 Protection: Synthesis via Aldrone Condensation, Optical Properties and 1,3‐Dipolar Cycloaddition Reaction

Debnath,

Roy,

Borah

et al. 2023

Chemistry An Asian Journal

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Abstractperi‐Annulation of naphthalane, an important tool for realization of wide range of functional materials, is presently accomplished with limited few functional groups like imide, amide and diamine‐derivative (perimidine). To increase the diversity, we have incorporated α‐keto aldonitrone as a new functional group, and herein report about five peri‐naphthoisatogens (PNTIs) dyes. The synthesis were accomplished using an unusual reaction of aromatic nitro group, which is nucleophilic attack of a C‐nucleophile (enol) to the N‐atom of nitro group. In five different 5‐alkylamino‐8‐nitro‐1‐acetylnaphthalenes, intramolecular acid‐catalyzed nucleophilic attack of enol moiety to the N‐atom of nitro group produced α‐keto aldonitrone via addition‐elimination mechanism. The PNTIs showed characteristics of 1,3‐dipole and reacted with ethyl acrylate to produce isoxazolidine ring, which subsequently converted into aza phenalenone derivative via ring cleavage. Both the PNTI and the corresponding derivative strongly absorb in the visible region, displaying absorption maximum at 551 and 561 nm (in CHCl3) respectively. Compared to the popular analogous dye naphthalene monoimides, PNTIs showed bathochromic shift of absorption maximum by more than 100 nm. The emission maximum for the PNTI and its derivative in chloroform were observed at 594 and 635 nm respectively.

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Emissive triphenylamine functionalised 1,8-naphthalimide and naphthalene diimide fluorophores: aggregation, computation and biological studies

Ramírez Lázaro,

Sigurvinsson,

Curtin

et al. 2025

J. Mater. Chem. B

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Triphenylamine-equipped 1,8-naphthaolactam: a versatile scaffold for the custom design of efficient subcellular imaging agents

Abstract: NP-TPA-Tars exhibits bright emission in various states with large Stokes and facile targeted modifications, and has improved imaging efficacy, better photostability than their commercial counterparts in imaging of targeted subcellular structures.

Cited by 3 publications

References 44 publications

Exploring the Transformation of Static Random Access Memory to Write-Once-Read-Many-Times Memory Behavior in Imidazole–Triphenylamine-Based Devices

Exploring the Transformation of Static Random Access Memory to Write-Once-Read-Many-Times Memory Behavior in Imidazole–Triphenylamine-Based Devices

Stable peri‐Naphthoisatogens without C2 Protection: Synthesis via Aldrone Condensation, Optical Properties and 1,3‐Dipolar Cycloaddition Reaction

Emissive triphenylamine functionalised 1,8-naphthalimide and naphthalene diimide fluorophores: aggregation, computation and biological studies

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