Customising excitation properties of polycyclic aromatic hydrocarbons by rational positional heteroatom doping: the<i>peri</i>-xanthenoxanthene (PXX) case

Valentini, Cataldo; Gowland, Duncan; Bezzu, C. Grazia; Romito, Deborah; Demitri, Nicola; Bonini, Nicola; Bonifazi, Davide

doi:10.1039/d2sc01038k

Cited by 8 publications

(14 citation statements)

References 55 publications

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“…). 13 C NMR (75 MHz, CDCl3) δ 157. 94, 153.99, 136.12, 129.71, 129.33, 124.42, 116.78, 115.15, 108.86, 105.55, 68.14, 31.75, 29.35, 25.92, 22.76, 14.20.…”

Section: -(Hexyloxy)naphthalen-2-ol (9)mentioning

confidence: 99%

“…(3.147g, 12.9 mmol, 64% 4H), 1.03 -0.87 (t, J = 7.0 Hz, 3H). 13 C NMR (75 MHz, CDCl3) δ 147. 25, 146.33, 129.97, 129.45, 126.87, 126.75, 124.62, 124.21, 109.53, 106.65, 68.92, 31.38, 28.83, 25.52, 22.38, 13.76.…”

Section: Template For Organic Materials Thiemementioning

confidence: 99%

“…(t, J = 6.8 Hz, 6H). 13 C NMR (75 MHz, CDCl3) δ 158. 55, 153.33, 134.96, 130.87, 129.86, 124.69, 116.34, 115.09, 110.44, 104.16, 67.85, 31.61, 28.99, 25.70, 22.61, 14.06.…”

Section: General Procedures For the Synthesis Of DI Hexylated Binolesmentioning

confidence: 99%

“…(m, 4H), 1.40 -1.37 (m, 8H), 0.93 (t, J = 7.0 Hz, 6H). 13 C NMR (126 MHz, THF-d8) δ 145. 28, 142.94, 141.51, 127.62, 127.40, 123.61, 121.31, 119.49, 116.46, 111.54, 71.24, 32.78, 30.75, 26.80, 23.72, 14.58.…”

Section: 3´-bis(hexyloxy)-[11'-binaphthalene]-22'-diol (12)mentioning

confidence: 99%

“…A 27, 152.71, 137.56, 131.31, 129.20, 129.13, 128.59, 128.31, 128.20, 128.05, 121.14, 116.62, 110.01, 107.99, 71.02, 70.70, 32.16, 30.05, 26.28, 23.22, 14.42 4H), 0.89 (t, J = 6.9 Hz, 3H). 13 C NMR (75 MHz, DMSO-d6) δ 156. 72, 154.24, 137.17, 131.20, 129.42, 128.90, 128.45, 128.01, 127.82, 127.74, 118.74, 115.54, 107.55, 69.17, 68.92, 31.10, 29.21, 25.19, 22.14, 13.98.…”

Section: -(Benzyloxy)-1-bromo-2-(hexyloxy)naphthalene (16)mentioning

confidence: 99%

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HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

et al. 2022

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A series of novel O-doped polycyclic aromatic hydrocarbons (PAHs), bearing a different number of electron donating alkoxy substituents, has been prepared using a novel copper-promoted anaerobic protocol for the cyclisation of highly electron rich peri-xanthenoxanthene (PXX) molecular modules. The effect of the number and position of the alkoxy substituents on the optoelectronic properties has thus been investigated, unveiling p-type semiconducting properties. All molecules displayed a significant colour change upon oxidation, suggesting that these compounds can be used to devise chromogenic materials to engineer electrochromic devices.

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“…). 13 C NMR (75 MHz, CDCl3) δ 157. 94, 153.99, 136.12, 129.71, 129.33, 124.42, 116.78, 115.15, 108.86, 105.55, 68.14, 31.75, 29.35, 25.92, 22.76, 14.20.…”

Section: -(Hexyloxy)naphthalen-2-ol (9)mentioning

confidence: 99%

Section: Template For Organic Materials Thiemementioning

confidence: 99%

“…(t, J = 6.8 Hz, 6H). 13 C NMR (75 MHz, CDCl3) δ 158. 55, 153.33, 134.96, 130.87, 129.86, 124.69, 116.34, 115.09, 110.44, 104.16, 67.85, 31.61, 28.99, 25.70, 22.61, 14.06.…”

Section: General Procedures For the Synthesis Of DI Hexylated Binolesmentioning

confidence: 99%

Section: 3´-bis(hexyloxy)-[11'-binaphthalene]-22'-diol (12)mentioning

confidence: 99%

Section: -(Benzyloxy)-1-bromo-2-(hexyloxy)naphthalene (16)mentioning

confidence: 99%

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HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

et al. 2022

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Furan‐Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

et al. 2022

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Lateral furan-expansion of polycyclic aromatics, which enables multiple O-doping and peripheral edge evolution of rylenes, is developed for the first time. Tetrafuranylperylene TPF-4CN and octafuranylquaterrylene OFQ-8CN were prepared as model compounds bearing unique fjord edge topology and helical conformations. Compared to TPF-4CN, the higher congener OFQ-8CN displays a largely red-shifted ( � 333 nm) and intensified absorption band (λ max = 829 nm) as well as a narrowed electrochemical band gap ( � 1.08 eV) due to its pronounced π-delocalization and emerging of open-shell diradicaloid upon the increase of fjord edge length. Moreover, strong circular dichroism signals in a broad range until 900 nm are observed for open-shell chiral OFQ-8CN, owing to the excellent conformational stability of its central bis(tetraoxa[5]helicene) fragments. Our studies provide insights into the relationships between edge topologies and (chir)optoelectronic properties for this novel type of O-doped PAHs.

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Furan‐Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

et al. 2022

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Customising excitation properties of polycyclic aromatic hydrocarbons by rational positional heteroatom doping: theperi-xanthenoxanthene (PXX) case

Abstract: In this paper we tackle the challenge of gaining control of the photophysical properties of PAHs through a site-specific N-doping within the structural aromatic framework.

Cited by 8 publications

References 55 publications

HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

HOMO Energy-Level Lifting in p-Type O-Doped Graphenoids: Synthesis of Electrochromic Alkoxy-Decorated Xanthenoxanthenes

Furan‐Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

Furan‐Extended Helical Rylenes with Fjord Edge Topology and Tunable Optoelectronic Properties

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