TY - JOUR

T1 - Tuning optical properties of aromatic near-infrared fluorescent switch through engineering functional heterocycle on donor moiety

AU - Lu, Zhou

AU - Yin, Hang

AU - Wei, Qinhua

AU - Zhang, Suyin

AU - Sun, Shuoqi

AU - Liu, Jianyong

AU - Chen, Da

AU - Qin, Laishun

AU - Chen, Junsheng

N1 - Funding Information: This work was financially supported by the National Key R&D Program of China (No. 2022YFB3503600 ), National Natural Science Foundation of China (NSFC) (No. 12275262 , 51972291 ), Natural Science Foundation of Zhejiang Province (No. LQ23A050004 ), the China Association for Science and Technology Youth Talent Promotion Project ( 2022QNRC001-No. YESS20220358 ), the Fundamental Research Funds for the Provincial Universities of Zhejiang (No. 2023YW31 ), Science and Technology Innovation Activity Program for College Students in Zhejiang Province (New Seedling Talent Program) Project , China Science and Technology Cloud, and the Open Fund of the State Key Laboratory of Molecular Reaction Dynamics in DICP, CAS . J. C. acknowledges support from the Novo Nordisk Foundation ( NNF22OC0073582 ). We gratefully acknowledge HZWTECH for providing computation facilities. Publisher Copyright: © 2024

PY - 2024

Y1 - 2024

N2 - Near-infrared (NIR) emissive fluorophores with donor−acceptor−donor (D−A−D) structures are attractive for deep tissue in vivo bioimaging and sensing, owing to their low background autofluorescence and deep penetration depth. In this study, we constructed a series of nitric oxide (NO)-responsive fluorescent switches with D−A−D structure, in which functional heterocycles act as donor moiety, resulting in the modification of fluorescence wavelengths from NIR-I (750–950 nm) to NIR-II (1000–1700 nm) region. Specifically, the NIR-I fluorescence can be achieved by using furan, thiophene and selenophene as the donor moiety. By using pyrrole as the donor moiety, NIR-II fluorescence can be achieved due to the strong N–H⋯N hydrogen bond interaction and tunable intramolecular charge transfer (ICT) process. Based on our findings, tailoring electronegativity of donor moiety could controllably tune the fluorescence wavelength from NIR-I to NIR-II region, proposing a practical design strategy for developing NIR-II fluorescent switches.

AB - Near-infrared (NIR) emissive fluorophores with donor−acceptor−donor (D−A−D) structures are attractive for deep tissue in vivo bioimaging and sensing, owing to their low background autofluorescence and deep penetration depth. In this study, we constructed a series of nitric oxide (NO)-responsive fluorescent switches with D−A−D structure, in which functional heterocycles act as donor moiety, resulting in the modification of fluorescence wavelengths from NIR-I (750–950 nm) to NIR-II (1000–1700 nm) region. Specifically, the NIR-I fluorescence can be achieved by using furan, thiophene and selenophene as the donor moiety. By using pyrrole as the donor moiety, NIR-II fluorescence can be achieved due to the strong N–H⋯N hydrogen bond interaction and tunable intramolecular charge transfer (ICT) process. Based on our findings, tailoring electronegativity of donor moiety could controllably tune the fluorescence wavelength from NIR-I to NIR-II region, proposing a practical design strategy for developing NIR-II fluorescent switches.

KW - Density functional theory

KW - Intramolecular charge transfer

KW - Near-infrared fluorescent switches

KW - NO detection

KW - Tuning optical properties

U2 - 10.1016/j.dyepig.2024.112044

DO - 10.1016/j.dyepig.2024.112044

M3 - Journal article

AN - SCOPUS:85186253988

VL - 224

JO - Dyes and Pigments

JF - Dyes and Pigments

SN - 0143-7208

M1 - 112044

ER -