Synthesis, Structures, and Optical Properties of Aza[4]helicenes

Zheng, Yuanhui; Lu, Haiyan; Li, Meng; Chen, Chuan‐Feng

doi:10.1002/ejoc.201300002

Cited by 31 publications

(22 citation statements)

References 69 publications

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“…In addition, they all exhibited several weak absorptions in the range of 370-390 nm, which were characteristic absorption of helicenes. [26] As for HTPI and HIPD, the weak absorption bands in the range of 400-420 nm were assigned to the intramolecular charge transfer (ICT) transition from indole group to anthracene group or quinoline group. [27] Redshifts for HTPI, HBTNI, HIPD and HPI in films compared to those in hexane were found.…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

Indole‐Based Aza[n]helicenes (n=5, 6) with Violet‐Blue Fluorescence and Two‐Photon Absorption (TPA)

Liu

et al. 2020

ChemPlusChem

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A series of indole-based helicenes, namely, 15-hexyl-15Htetraphenyl[1,2-e]indole (HTPI), 14-hexyl-14H-benzo[4',5']thieno [2',3':7,8]naphtha[1,2-e]indole (HBTNI), 7-hexyl-7H-indolo [5,4-k] phenanthridine (HIPD) and 3-hexyl-3H-phenanthro[4,3-e]indole (HPI) were successfully synthesized by three-or four-step reactions. They exhibited good solubility and high thermal stability of T d = 247, 388, 294 and 251°C, respectively. These compounds emit violet-blue light with maximum emission peaks at 415, 397, 397 and 391 nm in hexane. Among them, HBTNI had excellent thermal stability, narrow and sharp emission peaks, and highest photoluminescence quantum yield (0.32). Thus, HBTNI was an ideal candidate for the violet-blue emitters of OLEDs. Furthermore, the four compounds had twophoton absorption and two-photon excited fluorescence. HTPI showed the maximum TPA with the TPA cross-section (δ) of 171.5 GM at 770 nm. They were rare examples of helicenes with both violet-blue emission and TPA. J = 8.4 Hz, 1H; ArÀ H), 7.80 (d, J = 8.4 Hz, 1H; ArÀ H), 7.75 (d, J = 8.8 Hz, 1H; ArÀ H), 7.67-7.61 (m, 2H; ArÀ H), 7.54 (t, J = 7.2 Hz, 1H; ArÀ H), 7.43 (t, J = 8 Hz, 1H; ArÀ H), 7.01 (d, J = 2.8 Hz, 1H; Hexyl-H), 6.98 (d, J = 3.2 Hz, 1H; ArÀ H), 4.15 (t, J = 7.2 Hz, 2H; Hexyl-H), 1.85 (t, J = 7.2 Hz, 2H; Hexyl-H), 1.29 (s, 6H; Hexyl-H), 0.86 (t, J = 6.8 Hz, 3H; Hexyl-H) ppm. 13 C NMR (400 MHz, CDCl 3 ): δ =

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Section: Electrochemical Propertiesmentioning

confidence: 99%

Indole‐Based Aza[n]helicenes (n=5, 6) with Violet‐Blue Fluorescence and Two‐Photon Absorption (TPA)

Liu

et al. 2020

ChemPlusChem

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“…catalyzed cyclization to facilitate the construction of phenanthridines. Various Brønsted acids such as TfOH, [8a,b] trifluoroacetic acid [8c,d] as well as Lewis acid In(OTf) 3 [8e] have also been employed to achieve this process. Although considerable progress has been gained in the above examples, several drawbacks including expensive transition‐metal catalysts, corrosive reagents and high temperature condition, etc.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Decarboxylative Cyclization of α‐Amino‐Oxy Acids to Access Phenanthridine Derivatives

Zhan

Dai

Zhu

et al. 2022

Chemistry An Asian Journal

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Phenanthridines are a class of useful heterocycles in the field of drug development. In this work, a method via electrochemical decarboxylative cyclization of α‐amino‐oxy acids to access phenanthridine derivatives was developed. This reaction proceeded through iminyl radical formation cascade intramolecular cyclization from readily available materials under environmentally friendly conditions. A wide range of phenanthridine derivatives were obtained in moderate to high yields.

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“…[1][2][3][4][5][6][7][8][9][10] Various synthetic routes have been developed for the synthesis of simple helicenes, heterohelicenes, functionalized helicenes, and multi-helicene structures. [11][12][13][14][15][16][17] Multifunctional helicenes and their derivatives can play a key role in improving the photophysical and optoelectronic properties of twisted helical units. [18][19][20][21][22][23][24][25][26][27][28][29][30] Design and synthesis of such multifunctional helicene is one of the challenging and interesting areas.…”

Section: Introductionmentioning

confidence: 99%

Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

Soni

Soman

2022

Asian J Org Chem

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Coumarin containing hetero [n]helicene like molecules were synthesized using three component Povarov reaction followed by two dehydrogenation steps in good yields. Synthesis and photophysical properties of coumarin containing multifunctional helicene like molecules were found to be affected by substitution on pendant phenyl ring. Coumarin containing hetero[6]helicene like derivative 10 f showed bright yellow emission in solution, thin film, and solid state. Coumarin containing hetero[6]helicene like compound 13 e showed bright blue emission in solution, thin film, and solid state. The structures of intermediate compounds were confirmed by a single crystal X-ray analysis. These structures were compared with DFT optimized structures for the helicity parameters. DFT calculations provided good correlation with observed photophysical properties of compounds 10 f and 13 e.

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Synthesis, Structures, and Optical Properties of Aza[4]helicenes

Cited by 31 publications

References 69 publications

Indole‐Based Aza[n]helicenes (n=5, 6) with Violet‐Blue Fluorescence and Two‐Photon Absorption (TPA)

Indole‐Based Aza[n]helicenes (n=5, 6) with Violet‐Blue Fluorescence and Two‐Photon Absorption (TPA)

Electrochemical Decarboxylative Cyclization of α‐Amino‐Oxy Acids to Access Phenanthridine Derivatives

Metal Free Synthesis of Coumarin Containing Hetero[n]helicene like Molecules with TICT and AIE Properties

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