BN-Isosteres of Nonacene with Antiaromatic B 2 C 4 and N 2 C 4 Heterocycles: Synthesis and Strong Luminescence
Embedding both boron and nitrogen into the backbone of acenes to generate their isoelectronic structures has significantly enriched the acene chemistry to offer appealing properties. However, only small BN-heteroacenes have been extensively investigated, with BN-heptacenes as the hitherto longest ho...
Saved in:
| Published in | Angewandte Chemie International Edition Vol. 63; no. 11; p. e202316596 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Germany
11.03.2024
|
| Subjects | |
| Online Access | Get full text |
Cover
Loading…
| Abstract | Embedding both boron and nitrogen into the backbone of acenes to generate their isoelectronic structures has significantly enriched the acene chemistry to offer appealing properties. However, only small BN-heteroacenes have been extensively investigated, with BN-heptacenes as the hitherto longest homologue. Herein, we report the synthesis of three new nonacene BN-isosteres via incorporating a pair of antiaromatic B
C
and N
C
heterocycles, representing a new length record for BN-heteroacenes. The distance between the B
C
and N
C
rings affects the contribution of the charge-separated resonance forms, leading to tunable antiaromaticity of the two heterocycles. The adjusted local antiaromaticity manifests substantial influence on the molecular orbital arrangement, and consequently, the radiative transition rate of BN-3 is greatly enhanced compared with BN-1 and BN-2, realizing a high fluorescence quantum yield of 92 %. This work provides a novel design concept of large acene BN-isosteres and reveals the importance of BN/CC isosterism on their luminescent properties. |
|---|---|
| AbstractList | Embedding both boron and nitrogen into the backbone of acenes to generate their isoelectronic structures has significantly enriched the acene chemistry to offer appealing properties. However, only small BN-heteroacenes have been extensively investigated, with BN-heptacenes as the hitherto longest homologue. Herein, we report the synthesis of three new nonacene BN-isosteres via incorporating a pair of antiaromatic B
C
and N
C
heterocycles, representing a new length record for BN-heteroacenes. The distance between the B
C
and N
C
rings affects the contribution of the charge-separated resonance forms, leading to tunable antiaromaticity of the two heterocycles. The adjusted local antiaromaticity manifests substantial influence on the molecular orbital arrangement, and consequently, the radiative transition rate of BN-3 is greatly enhanced compared with BN-1 and BN-2, realizing a high fluorescence quantum yield of 92 %. This work provides a novel design concept of large acene BN-isosteres and reveals the importance of BN/CC isosterism on their luminescent properties. |
| Author | Chang, Zhi-Dong Chen, Cheng Huang, Yan-Bo Guo, Yong-Kang Wang, Xiao-Ye |
| Author_xml | – sequence: 1 givenname: Cheng surname: Chen fullname: Chen, Cheng organization: State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 300071, Tianjin, China – sequence: 2 givenname: Zhi-Dong surname: Chang fullname: Chang, Zhi-Dong organization: State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 300071, Tianjin, China – sequence: 3 givenname: Yong-Kang surname: Guo fullname: Guo, Yong-Kang organization: State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 300071, Tianjin, China – sequence: 4 givenname: Yan-Bo surname: Huang fullname: Huang, Yan-Bo organization: State Key Laboratory of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, 300071, Tianjin, China – sequence: 5 givenname: Xiao-Ye orcidid: 0000-0003-3540-0277 surname: Wang fullname: Wang, Xiao-Ye organization: Beijing National Laboratory for Molecular Sciences, Beijing, 100190, China |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38216533$$D View this record in MEDLINE/PubMed |
| BookMark | eNqFjsEOwUAURSdCUPyCvB9o0naoxg4hJNJN7ZsxXhnRNzJvRPr3RFhb3bs45-YGok2WsCX68TSJQzmbyZ4ImK9RlGRZlHZFT2ZJnE6l7Ata5uGOLXt0yGAryC0pjYTwNP4CC_JGOVsrbzQsIYEVTEDRCfJv3-LbtLrRN-Q5FA35C7LhD1N4Z-kM-0dtCPk9qnEoOpW6MY6-ORDjzfqw2ob3x7HGU3l3plauKX8H5V_gBSLbRj4 |
| ContentType | Journal Article |
| Copyright | 2024 Wiley-VCH GmbH. |
| Copyright_xml | – notice: 2024 Wiley-VCH GmbH. |
| DBID | NPM |
| DatabaseName | PubMed |
| DatabaseTitle | PubMed |
| DatabaseTitleList | PubMed |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: https://proxy.k.utb.cz/login?url=http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1521-3773 |
| ExternalDocumentID | 38216533 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: National Natural Science Foundation of China grantid: 22071120 – fundername: National Natural Science Foundation of China grantid: 92256304 – fundername: National Key Research and Development Program of China grantid: 2020YFA0711500 – fundername: National Natural Science Foundation of China grantid: 22221002 – fundername: Beijing National Laboratory for Molecular Sciences grantid: BNLMS2023013 |
| GroupedDBID | --- -DZ -~X .3N .GA 05W 0R~ 10A 1L6 1OB 1OC 1ZS 23M 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5RE 5VS 66C 6TJ 702 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHHS AANLZ AAONW AAXRX AAZKR ABCQN ABCUV ABEML ABIJN ABLJU ABPPZ ABPVW ACAHQ ACCFJ ACCZN ACFBH ACGFS ACIWK ACNCT ACPOU ACPRK ACSCC ACXBN ACXQS ADBBV ADEOM ADIZJ ADKYN ADMGS ADOZA ADXAS ADZMN ADZOD AEEZP AEIGN AEIMD AEQDE AEUQT AEUYR AFBPY AFFNX AFFPM AFGKR AFPWT AFRAH AFZJQ AHBTC AHMBA AITYG AIURR AIWBW AJBDE AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALUQN AMBMR AMYDB ATUGU AUFTA AZBYB AZVAB B-7 BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BTSUX BY8 CS3 D-E D-F D0L DCZOG DPXWK DR1 DR2 DRFUL DRSTM EBS F00 F01 F04 F5P G-S G.N GNP GODZA H.T H.X HBH HGLYW HHY HHZ HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB NPM O66 O9- OIG P2P P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RNS ROL RWI RX1 RYL SUPJJ TN5 UB1 UPT UQL V2E VQA W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WRC WXSBR WYISQ XG1 XPP XSW XV2 YZZ ZZTAW ~IA ~KM ~WT |
| ID | FETCH-pubmed_primary_382165333 |
| IngestDate | Sat Sep 28 08:07:23 EDT 2024 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 11 |
| Keywords | acenes luminescence antiaromaticity B,N-heterocycles |
| Language | English |
| License | 2024 Wiley-VCH GmbH. |
| LinkModel | OpenURL |
| MergedId | FETCHMERGED-pubmed_primary_382165333 |
| ORCID | 0000-0003-3540-0277 |
| PMID | 38216533 |
| ParticipantIDs | pubmed_primary_38216533 |
| PublicationCentury | 2000 |
| PublicationDate | 2024-Mar-11 |
| PublicationDateYYYYMMDD | 2024-03-11 |
| PublicationDate_xml | – month: 03 year: 2024 text: 2024-Mar-11 day: 11 |
| PublicationDecade | 2020 |
| PublicationPlace | Germany |
| PublicationPlace_xml | – name: Germany |
| PublicationTitle | Angewandte Chemie International Edition |
| PublicationTitleAlternate | Angew Chem Int Ed Engl |
| PublicationYear | 2024 |
| SSID | ssj0028806 |
| Score | 4.584139 |
| Snippet | Embedding both boron and nitrogen into the backbone of acenes to generate their isoelectronic structures has significantly enriched the acene chemistry to... |
| SourceID | pubmed |
| SourceType | Index Database |
| StartPage | e202316596 |
| Title | BN-Isosteres of Nonacene with Antiaromatic B 2 C 4 and N 2 C 4 Heterocycles: Synthesis and Strong Luminescence |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/38216533 |
| Volume | 63 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnZ3JTsMwEIatwgUuiH1HPnCLjLKTcGvTQtlyYJGAC2SxSw9NqtIIwdMzXtJaFUjAJbXsNEr6pSN7PPMPQocWC1kaWgExMz8kbppYJKGOR8JjmwV5mgW52C64jv3uvXvx4D00Gi9a1FI1To-yz2_zSv5DFfqAK8-S_QPZyUWhA9rAF45AGI6_YtyKyfkbz9IYSenYGKbVGRgv6V1tFvDvHZVSk7Vl2EZkuGKvIFbtLg-FKbOPOjDu9qOA6SBXKBHxnNxJ3jOuqgGPjM9o_XZMlJd79D3hyQCGEB2gM87FTt7X9_gjlQXCP3taTIE0NU-vfdIupwNnlfDgPkIXuUym_d1KfeExKUir1F0WtstjtpRJpcrM2haYNlnEpLbDytCp983SrCrlNd4t35O1bzWww4Eg6wQ2jEpBjRn17HpoDs05Fg_5bN9M5MVssF28hFV9zszKQsww7pbRkloa4KbkvIIatFhFC1FdkW8NFTpvXDJc88acN9Z54xa2cYRdDIRwrNo67xM8oS3OkbSxTnsdHZx27qIukbf7PJTCJM_1gzgbaL4oC7qFcBqmtukx5meJ5-aWkzBm-llohjkzHcc3t9HmDxfZ-XFkFy1Oqe6h-fGoovswNRunB-L3_QIz40AN |
| link.rule.ids | 315,786,790 |
| linkProvider | Wiley-Blackwell |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=BN-Isosteres+of+Nonacene+with+Antiaromatic+B+2+C+4+and+N+2+C+4+Heterocycles%3A+Synthesis+and+Strong+Luminescence&rft.jtitle=Angewandte+Chemie+International+Edition&rft.au=Chen%2C+Cheng&rft.au=Chang%2C+Zhi-Dong&rft.au=Guo%2C+Yong-Kang&rft.au=Huang%2C+Yan-Bo&rft.date=2024-03-11&rft.eissn=1521-3773&rft.volume=63&rft.issue=11&rft.spage=e202316596&rft_id=info%3Apmid%2F38216533&rft.externalDocID=38216533 |