Color-tunable emission from violet-blue to pure-blue based on 5,9-disubstituted pyrene derivatives<i>via</i>engineering of aryl-side groups

Xie, Fuli; Yang, Xilin; Jin, Pengcheng; Wang, Xiao-Tian; Ran, Huijuan; Zheng, Rong; Zheng, Lei; Zhang, Hailu; Su, Shi‐Jian; Hu, Jian‐Yong

doi:10.1039/d2tc01723g

Cited by 11 publications

(14 citation statements)

References 62 publications

(81 reference statements)

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“…1 H NMR (250 MHz, CDCl 3 ): δ 8.66 (s, 2H), 7.54−7.60 (m, 2H), 7.17−7.35 (m, 6H), 2.58 (s, 6H). 13 (27), 341 (100, M + ), 305 (13), 304 (27), 303 (10), 277 (11), 276 (21) (19), 425 (55, M + ), 413 (11), 412 (34), 411 (31), 410 (100), 197 (14), 169 (13), 73 (15), 57 (20), 41 (84), 39 (13). (7), 286 (13), 266 (7), 175 (8) If not otherwise stated, an oven-dried pressure tube charged with the respective 3,5diarylalkynyl-4-chloropyridine 1a-l (200 mg, 1.0 equiv), K 3 PO 4 (2.0 equiv), PdCl 2 (MeCN) 2 (0.05 equiv), SPhos (0.1 equiv), and 3thienylboronic acid (2.0 equiv) was evacuated and backfilled with argon for 3 times.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…7.92 (dd, J = 3.0 Hz, J = 1.3 Hz, 1H), 7.65 (dd, J = 4.9 Hz, J = 1.3 Hz, 1H), 7.29−7.48 (m, 11H). 13 (51), 207 (15), 163 (22), 150 (15), 135 (15), 126 (29), 77 (77), 76 (14), 74 (16), 73 (74), 63 (20), 51 (27), 45 (36), 39 (23). (46), 387 (11), 375 (15), 374 (50), 373 (42), 372 (12), 359 (13), 187 (10), 186 (9), 179 (8), 170 (8).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…According to general procedure A, title compound 2h was isolated as a yellow solid in 76% yield (170. (41), 378 (14), 377 (17), 376 (6), 375 (7), 368 (9), 188 (7). HRMS (EI) m/z: [M + ] calcd for C 25 H 13 NF 2 S, 397.0731; found, 397.0715.…”

Section: 4′-((4-(thiophen-3-yl)pyridine-35-diyl)bis(ethin-21-diyl))bi...mentioning

confidence: 99%

“…, 395 (41), 378 (14), 377 (17), 376 (6), 375 (7), 368 (9), 188 (7). HRMS (EI) m/z: [M + ] calcd for C 25 H 13 NF 2 S, 397.0731; found, 397.0715.…”

Section: 5-bis((2-fluorophenyl)ethynyl)-4-(thiophen-3-yl)pyridine (2j)mentioning

confidence: 99%

“…Among polycyclic aromatic hydrocarbons (PAHs), pyrene is one of the most intensively investigated peri-fused PAH motifs in interdisciplinary fields of science owing to its unique characteristics, like unusual long excited state lifetime, excimer/exciplex formation, high charge-carrier mobility, chemical stability, and sensing features . Inspired by these properties and the flexible peripheral modification potential, chemists are continuously engaged in the development of simple and efficient synthetic strategies to prepare diverse libraries of pyrene derivatives with custom-made properties for applications in analytics, biomedicine, and materials science. − Along with direct and indirect methods for the selective peripheral (un)symmetric functionalization of the K and non-K regions of pyrene, − which exhibit strong position and functional group-dependent photophysical properties, − the doping of heteroatoms into the π-conjugated framework is one of the most fundamental strategies to effectively tailor key electronic structural features and enhance desirable properties, including energy levels, band-gaps, and n- or p-type semiconductor characteristics. − …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Molenda,

Polkaehn,

Argüello Cordero

et al. 2023

J. Org. Chem.

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Thieno[2′,3′,4′:4,5]naphtho [1,8-cd]pyridines, S,N-doped pyrene analogs, were prepared by combination of Pd catalyzed cross-coupling reactions and acid-mediated cycloisomerization. The modular scope of the synthesis allowed for access to a variety of functionalized derivatives. The photophysical properties have been studied in detail by steady-state and femtosecond transient absorption accompanied by cyclic voltammetry and (TD)-DFT calculations. The introduction of a five-membered thiophene into the 2-azapyrene scaffold leads to redshifted emission and substantial effects on the excited state dynamics, e.g., quantum yield, lifetime, decay rates, and the ISC ability, which can be further tuned by the substitution pattern of the heterocyclic scaffold.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: 4′-((4-(thiophen-3-yl)pyridine-35-diyl)bis(ethin-21-diyl))bi...mentioning

confidence: 99%

“…, 395 (41), 378 (14), 377 (17), 376 (6), 375 (7), 368 (9), 188 (7). HRMS (EI) m/z: [M + ] calcd for C 25 H 13 NF 2 S, 397.0731; found, 397.0715.…”

Section: 5-bis((2-fluorophenyl)ethynyl)-4-(thiophen-3-yl)pyridine (2j)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Molenda,

Polkaehn,

Argüello Cordero

et al. 2023

J. Org. Chem.

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Achieving Simultaneously Ultrahigh Brightness, Extremely Low Efficiency Roll‐Off and Ultralong Lifetime of Blue Fluorescent OLEDs by Using Donor–Acceptor‐Type 5,9‐Diarylamine Functionalized Pyrenes

Xie

Yang

Jin

et al. 2022

Advanced Optical Materials

Self Cite

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In this study, four new donor–acceptor (DA)‐type blue emitters (Py(5,9)BDPA, Py(5,9)BMTBA, Py(5,9)BDTBA, and Py (5,9)BTTBA) are developed by adopting benzene ring as A units and the diphenylamine (DPA) with different electron‐donating substituents as D units connected to 1,3‐positions and 5,9‐positions of pyrene ring, respectively. Gratifyingly, single‐crystal X‐ray analysis of the compounds demonstrates that the disgusting excimers in solid‐state could be effectively inhibited by the D units even the unsubstituted DPA resorting to the superiority of introducing D‐units at the 5,9‐positions of pyrene. The corresponding doped devices display ultrahigh luminance and extremely low efficiency roll‐off characteristics, especially for Py(5,9)BDPA, a roll‐off of external quantum efficiency is less than 4.9% when the luminance is up to 30 000 cd m−2, also showing good operation stability of devices. The optimized advanced device of the representative blue emitter Py(5,9)BDPA with a low manufacturing cost achieves extremely long LT95 (lifetime to 95% of the initial luminance) of 74 and 534 h at an initial luminance of 3000 and 1000 cd m−2, respectively. The ultralong lifetime of the emitter Py(5,9)BDPA is eye‐catching in the reported blue OLED lifetime and further demonstrates the practical applications in display and lighting of these DA‐type pyrene‐based blue emitters.

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Novel Y-shaped multi-stimuli responsive pyrene substituted quinoxaline and pyridopyrazine-based push-pull molecules showing solvatochromism, aggregation induced excimer emission, acidofluorochromism and moisture detection

Lamoria

Milton

2023

Dyes and Pigments

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Color-tunable emission from violet-blue to pure-blue based on 5,9-disubstituted pyrene derivativesviaengineering of aryl-side groups

Abstract: It is special necessary to explore the influence of side group linked to pyrene core on the photophysical properties for constructing efficient pyrene-based blue-emitting materials. In this study, a series...

Cited by 11 publications

References 62 publications

Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Synthesis and Properties of Thieno[2′,3′,4′:4,5]naphtho[1,8-cd]pyridines

Achieving Simultaneously Ultrahigh Brightness, Extremely Low Efficiency Roll‐Off and Ultralong Lifetime of Blue Fluorescent OLEDs by Using Donor–Acceptor‐Type 5,9‐Diarylamine Functionalized Pyrenes

Novel Y-shaped multi-stimuli responsive pyrene substituted quinoxaline and pyridopyrazine-based push-pull molecules showing solvatochromism, aggregation induced excimer emission, acidofluorochromism and moisture detection

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