Solvent-dependent fluorescence behaviour of imide-fused [n]phenacenes (n = 3, 5, 7)

Keito Nose; Kaito Yoshioka; Minoru Yamaji; Fumito Tani; Kenta Goto; Hideki Okamoto

doi:10.1039/d2ra07771j

Solvent-dependent fluorescence behaviour of imide-fused [n]phenacenes (n = 3, 5, 7)

Keito Nose, Kaito Yoshioka, Minoru Yamaji, Fumito Tani, Kenta Goto, Hideki Okamoto

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Imide-fused [n]phenacenes (nPDIs, n = 3, 5, 7) were systematically synthesised and their electronic features were investigated by electrochemical and electronic spectral measurements. nPDIs showed two reduction waves attributed to formation of radical ions and dianions. 3PDI produced blue fluorescence independent of solvent polarity. In contrast, 5PDI and 7PDI displayed marked positive solvatofluorochromism due to intramolecular charge transfer characters between the imide moieties and phenacene p cores in the excited state. The spectral features were analyzed by the Lippert-Mataga relationship and theoretical calculations.

Original language	English
Pages (from-to)	4096-4101
Number of pages	6
Journal	RSC Advances
Volume	13
Issue number	6
DOIs	https://doi.org/10.1039/d2ra07771j
Publication status	Published - Jan 30 2023

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

Access to Document

10.1039/d2ra07771j

Cite this

@article{52fb1fd99c494b50a23e81569a584a02,

title = "Solvent-dependent fluorescence behaviour of imide-fused [n]phenacenes (n = 3, 5, 7)",

abstract = "Imide-fused [n]phenacenes (nPDIs, n = 3, 5, 7) were systematically synthesised and their electronic features were investigated by electrochemical and electronic spectral measurements. nPDIs showed two reduction waves attributed to formation of radical ions and dianions. 3PDI produced blue fluorescence independent of solvent polarity. In contrast, 5PDI and 7PDI displayed marked positive solvatofluorochromism due to intramolecular charge transfer characters between the imide moieties and phenacene p cores in the excited state. The spectral features were analyzed by the Lippert-Mataga relationship and theoretical calculations.",

author = "Keito Nose and Kaito Yoshioka and Minoru Yamaji and Fumito Tani and Kenta Goto and Hideki Okamoto",

note = "Funding Information: The present study was supported by Grants-in-Aid for Scientific Research, KAKENHI, from JSPS, Japan (JP18H02043 and JP20K05648), and by the Cooperative Research Program of the {\textquoteleft}Network Joint Research Centre for Materials and Devices.{\textquoteright} Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = jan,

day = "30",

doi = "10.1039/d2ra07771j",

language = "English",

volume = "13",

pages = "4096--4101",

journal = "RSC Advances",

issn = "2046-2069",

publisher = "Royal Society of Chemistry",

number = "6",

}

TY - JOUR

T1 - Solvent-dependent fluorescence behaviour of imide-fused [n]phenacenes (n = 3, 5, 7)

AU - Nose, Keito

AU - Yoshioka, Kaito

AU - Yamaji, Minoru

AU - Tani, Fumito

AU - Goto, Kenta

AU - Okamoto, Hideki

N1 - Funding Information: The present study was supported by Grants-in-Aid for Scientific Research, KAKENHI, from JSPS, Japan (JP18H02043 and JP20K05648), and by the Cooperative Research Program of the ‘Network Joint Research Centre for Materials and Devices.’ Publisher Copyright: © 2023 The Royal Society of Chemistry.

PY - 2023/1/30

Y1 - 2023/1/30

N2 - Imide-fused [n]phenacenes (nPDIs, n = 3, 5, 7) were systematically synthesised and their electronic features were investigated by electrochemical and electronic spectral measurements. nPDIs showed two reduction waves attributed to formation of radical ions and dianions. 3PDI produced blue fluorescence independent of solvent polarity. In contrast, 5PDI and 7PDI displayed marked positive solvatofluorochromism due to intramolecular charge transfer characters between the imide moieties and phenacene p cores in the excited state. The spectral features were analyzed by the Lippert-Mataga relationship and theoretical calculations.

AB - Imide-fused [n]phenacenes (nPDIs, n = 3, 5, 7) were systematically synthesised and their electronic features were investigated by electrochemical and electronic spectral measurements. nPDIs showed two reduction waves attributed to formation of radical ions and dianions. 3PDI produced blue fluorescence independent of solvent polarity. In contrast, 5PDI and 7PDI displayed marked positive solvatofluorochromism due to intramolecular charge transfer characters between the imide moieties and phenacene p cores in the excited state. The spectral features were analyzed by the Lippert-Mataga relationship and theoretical calculations.

UR - http://www.scopus.com/inward/record.url?scp=85147509394&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85147509394&partnerID=8YFLogxK

U2 - 10.1039/d2ra07771j

DO - 10.1039/d2ra07771j

M3 - Article

AN - SCOPUS:85147509394

SN - 2046-2069

VL - 13

SP - 4096

EP - 4101

JO - RSC Advances

JF - RSC Advances

IS - 6

ER -

Solvent-dependent fluorescence behaviour of imide-fused [n]phenacenes (n = 3, 5, 7)

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this