Cu-catalyzed C–H amination/Ullmann N-arylation domino reaction: a straightforward synthesis of 9,14-diaryl-9,14-dihydrodibenzo[a,c]phenazine

Wang, Huan; Zhang, Zhiyun; Zhou, Haitao; Wang, Tonghai; Su, Jianhua; Tong, Xiaofeng; Tian, He

doi:10.1039/c6cc01569g

Cited by 37 publications

(23 citation statements)

References 40 publications

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“…The syntheses of M x ‐M y were achieved using the copper‐catalyzed C−H amination/Ullmann N‐arylation domino reaction . The structures of all compounds were confirmed by X‐ray analysis (Figure c, and see details in Figures S1–S6 in the Supporting Information).…”

Section: Figurementioning

confidence: 91%

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Zhang

Chen

et al. 2018

Angew Chem Int Ed

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ortho-Methyl effects are exploited to tune steric hindrance between side-chain N,N'-diaryls and polycyclic dihydrodibenzo[a,c]phenazine, and in turn control the conformations of N,N'-diphenyl-dihydrodibenzo[a,c]phenazine (DPAC) and its ortho-methyl derivatives Mx-My (x=0, 1 or 2, y=1 or 2, x and y correlate with the number of methyl groups in the ortho-positiond of N,N'-diphenyl). The magnitude of steric hindrance increases as x and y increase, and the V-shaped dihydrodibenzo[a,c]phenazine skeleton is gradually tuned from a bent (DPAC) to planar (M2-M2) structure in the ground state. As a result, the relaxation of the excited-state structure of DPAC and its numerous analogues could be mimicked by model structures Mx-My, demonstrating for the first time the the conformation change from bent-to-planar and hence a large range of energy-gap tuning of polycyclic conjugated structures controlled by the steric hindrance.

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Section: Figurementioning

confidence: 91%

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Zhang

Chen

et al. 2018

Angew Chem Int Ed

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“…Thesyntheses of Mx-My were achieved using the coppercatalyzed C À Hamination/Ullmann N-arylation domino reaction. [6] Thestructures of all compounds were confirmed by Xray analysis (Figure 1c,and see details in Figures S1-S6 in the Supporting Information). TheV -shaped dihydrodibenzo-[a,c]phenazine skeleton of DPAC is bent along the N-N axis with an angle of V b % 1378 8 (Figure 1c), and the N,N'diphenyl rings and N-N axis of DPAC form as ymmetrical inverted U-shaped bay with bay angles the V S1 and V S2 around 1108 8 (see Figure S1a).…”

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confidence: 78%

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Zhang

Chen

et al. 2018

Angewandte Chemie

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ortho-Methyl effects are exploited to tune steric hindrance between side-chain N,N'-diaryls and polycyclic dihydrodibenzo[a,c]phenazine,a nd in turn control the conformations of N,N'-diphenyl-dihydrodibenzo[a,c]phenazine (DPAC)a nd its ortho-methyl derivatives Mx-My( x= 0, 1o r 2, y = 1o r2 ,xand yc orrelate with the number of methyl groups in the ortho-positiond of N,N'-diphenyl). The magnitude of steric hindrance increases as xand yincrease,and the Vshaped dihydrodibenzo[a,c]phenazine skeleton is gradually tuned from abent (DPAC)toplanar (M2-M2)structure in the ground state.A saresult, the relaxation of the excited-state structure of DPAC and its numerous analogues could be mimicked by model structures Mx-My, demonstrating for the first time the the conformation change from bent-to-planar and hence al arge range of energy-gap tuning of polycyclic conjugated structures controlled by the steric hindrance.

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“…The synthesis of DPAC‐OH and 4‐oxo‐4‐(prop‐2‐yn‐1‐ylamino)butanoic acid was according to previous research. [ 15 ] A mixture of 4‐oxo‐4‐(prop‐2‐yn‐1‐ylamino)butanoic acid (20.1 mg, 0.13 mmol), DPAC‐OH (50 mg, 0.108 mmol), EDC·HCl (25 mg, 0.13 mmol), and DMAP (16 mg, 0.13 mmol) in DCM (100 mL) was stirred at rt for 5 h, quenched with water, extracted with DCM, dried over MgSO 4 , filtered, concentrated, and purified by column chromatography on silica (PE:DCM = 1:1) to give a light yellow solid 45 mg. Yield: 57.6%. 1 H NMR (400 MHz, chloroform‐d) δ 8.74 (d, J = 8.3 Hz, 2H), 8.13–8.05 (m, 2H), 7.78–7.71 (m, 2H), 7.65 (t, J = 7.7 Hz, 2H), 7.56 (t, J = 7.5 Hz, 2H), 7.35 (s, 2H), 7.08–6.90 (m, 8H), 6.79 (t, J = 7.0 Hz, 1H), 5.76 (s, 1H), 4.92 (s, 2H), 3.98 (dd, J = 5.2, 2.6 Hz, 2H), 2.65 (t, J = 6.6 Hz, 2H), 2.43 (t, J = 6.7 Hz, 2H), 2.17 (t, J = 2.5 Hz, 1H).…”

Section: Methodsmentioning

confidence: 99%

Light‐Responsive Circularly Polarized Luminescence Polymers with INHIBIT Logic Function

Huang

Jin

et al. 2021

Advanced Optical Materials

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Dynamically tuning the emission of circularly polarized luminescence (CPL) materials through external stimuli is fascinating because of their fundamental and application interests. In this work, light‐responsive and luminescence‐tunable CPL‐active materials are synthesized by mixing achiral helical polymer containing vibration‐induced emission (VIE) molecules and spiropyran (SP) with a chiral helical polymer. Through regulating the distinct emission of VIE molecules and the reversible photoisomerization of SP, the dynamic Förster resonance energy transfer (FRET) can be explored to reversibly control the emission color of CPL in different states after light‐controlled isomerization. This project is the first comprehensive investigation of CPL‐active materials with VIE properties. Finally, taking the advantage of the multistimuli responsive CPL signal in different states, an “INHIBIT” logic gate with CPL signal output based on the combination of control of UV/vis light irradiation time and state alternation is constructed.

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Cu-catalyzed C–H amination/Ullmann N-arylation domino reaction: a straightforward synthesis of 9,14-diaryl-9,14-dihydrodibenzo[a,c]phenazine

Cited by 37 publications

References 40 publications

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Tuning the Conformation and Color of Conjugated Polyheterocyclic Skeletons by Installing ortho‐Methyl Groups

Light‐Responsive Circularly Polarized Luminescence Polymers with INHIBIT Logic Function

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