A Peri‐tetracene Diradicaloid: Synthesis and Properties
Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl...
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| Published in | Angewandte Chemie International Edition Vol. 57; no. 31; pp. 9697 - 9701 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
26.07.2018
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
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| Abstract | Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character (y0=51.5 % by calculation) and a small singlet–triplet gap (ΔES‐T=−2.5 kcal mol−1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3.
Synthesis of peri‐tetracene done: A stable peri‐tetracene derivative was obtained in crystalline form. It has an open‐shell singlet ground state with a moderate diradical character. It shows amphoteric redox behavior with a small optical and electrochemical energy gap. It is magnetically active and exhibits a small single–triplet excitation energy. It is globally aromatic. |
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| AbstractList | Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character (y0=51.5 % by calculation) and a small singlet–triplet gap (ΔES‐T=−2.5 kcal mol−1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3.
Synthesis of peri‐tetracene done: A stable peri‐tetracene derivative was obtained in crystalline form. It has an open‐shell singlet ground state with a moderate diradical character. It shows amphoteric redox behavior with a small optical and electrochemical energy gap. It is magnetically active and exhibits a small single–triplet excitation energy. It is globally aromatic. Peri-acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open-shell diradical character. Now, the successful synthesis and isolation of a stable peri-tetracene derivative PT-2ClPh is reported; four 2,6-dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X-ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open-shell singlet ground state with a moderate diradical character (y(0)=51.5% by calculation) and a small singlet-triplet gap (ES-T=-2.5kcalmol(-1) by SQUID measurement). It displays global aromatic character, which is different from the smaller-size bisanthene analogue BA-CF3. Peri-acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open-shell diradical character. Now, the successful synthesis and isolation of a stable peri-tetracene derivative PT-2ClPh is reported; four 2,6-dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X-ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open-shell singlet ground state with a moderate diradical character (y =51.5 % by calculation) and a small singlet-triplet gap (ΔE =-2.5 kcal mol by SQUID measurement). It displays global aromatic character, which is different from the smaller-size bisanthene analogue BA-CF3. Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character ( y 0 =51.5 % by calculation) and a small singlet–triplet gap (Δ E S‐T =−2.5 kcal mol −1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3 . Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell diradical character. Now, the successful synthesis and isolation of a stable peri‐tetracene derivative PT‐2ClPh is reported; four 2,6‐dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X‐ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open‐shell singlet ground state with a moderate diradical character (y0=51.5 % by calculation) and a small singlet–triplet gap (ΔES‐T=−2.5 kcal mol−1 by SQUID measurement). It displays global aromatic character, which is different from the smaller‐size bisanthene analogue BA‐CF3. Peri-acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open-shell diradical character. Now, the successful synthesis and isolation of a stable peri-tetracene derivative PT-2ClPh is reported; four 2,6-dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X-ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open-shell singlet ground state with a moderate diradical character (y0 =51.5 % by calculation) and a small singlet-triplet gap (ΔES-T =-2.5 kcal mol-1 by SQUID measurement). It displays global aromatic character, which is different from the smaller-size bisanthene analogue BA-CF3.Peri-acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open-shell diradical character. Now, the successful synthesis and isolation of a stable peri-tetracene derivative PT-2ClPh is reported; four 2,6-dichlorophenyl groups are attached onto the most reactive sites along the zigzag edges. The structure was confirmed by X-ray crystallographic analysis and its electronic properties were systematically investigated by both experiments and theoretical calculations. It exhibits an open-shell singlet ground state with a moderate diradical character (y0 =51.5 % by calculation) and a small singlet-triplet gap (ΔES-T =-2.5 kcal mol-1 by SQUID measurement). It displays global aromatic character, which is different from the smaller-size bisanthene analogue BA-CF3. |
| Author | Herng, Tun Seng Han, Yi Ni, Yong Ding, Jun Wu, Jishan Gopalakrishna, Tullimilli Y. Phan, Hoa Wu, Shaofei |
| Author_xml | – sequence: 1 givenname: Yong surname: Ni fullname: Ni, Yong organization: National University of Singapore – sequence: 2 givenname: Tullimilli Y. surname: Gopalakrishna fullname: Gopalakrishna, Tullimilli Y. organization: National University of Singapore – sequence: 3 givenname: Hoa surname: Phan fullname: Phan, Hoa organization: National University of Singapore – sequence: 4 givenname: Tun Seng surname: Herng fullname: Herng, Tun Seng organization: National University of Singapore – sequence: 5 givenname: Shaofei surname: Wu fullname: Wu, Shaofei organization: National University of Singapore – sequence: 6 givenname: Yi surname: Han fullname: Han, Yi organization: National University of Singapore – sequence: 7 givenname: Jun surname: Ding fullname: Ding, Jun organization: National University of Singapore – sequence: 8 givenname: Jishan orcidid: 0000-0002-8231-0437 surname: Wu fullname: Wu, Jishan email: chmwuj@nus.edu.sg organization: National University of Singapore |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29944208$$D View this record in MEDLINE/PubMed |
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| Keywords | EDGE STATE GRAPHENE NANORIBBONS POLYCYCLIC AROMATIC-HYDROCARBON HIGHER ACENES polycyclic aromatic hydrocarbons ORGANIC SEMICONDUCTORS SOLID-STATE SINGLET MOLECULES acenes zigzag edge BIRADICAL GROUND-STATE HEPTACENE diradicaloids peri-acene |
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| Snippet | Peri‐acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open‐shell... Peri-acenes are good model compounds for zigzag graphene nanoribbons, but their synthesis is extremely challenging owing to their intrinsic open-shell... |
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| SubjectTerms | acenes Chemistry Chemistry, Multidisciplinary Crystallography diradicaloids peri-acene Physical Sciences polycyclic aromatic hydrocarbons Science & Technology Synthesis zigzag edge |
| Title | A Peri‐tetracene Diradicaloid: Synthesis and Properties |
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