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Near infrared absorption/emission perylenebisimide fluorophores with geometry relaxation-induced large Stokes shift.

ABSTRACT: The dyes (P-1 and P-2) of perylenebisimide (PBI) conjugated with 2-(2-hydroxyphenyl)benzothiazole (HBT) were prepared by Sonogashira coupling reaction. The new compounds have special photophysical properties, such as near infrared absorption/emission and large Stokes shift. The UV-vis absorption (range from 651 nm to 690 nm) and emission wavelength (range from 732 nm to 756 nm) of P-1 and P-2 extend to near infrared range. Importantly, they have much larger Stokes shifts (range from 73 nm to 105 nm) compared with the conventional PBI derivatives, such as 7 (from 19 nm to 65 nm) and 9 (from 81 nm to 86 nm). TD-DFT calculation was used to rationalize UV-vis absorption, emission and especially large Stokes shift from the theoretical point of view. We found geometry relaxation of P-1 and P-2 in the excited state is an important reason for the origin of large Stokes shift besides intramolecular electron transfer (ICT).

SUBMITTER: Ma J

PROVIDER: S-EPMC9056887 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Near infrared absorption/emission perylenebisimide fluorophores with geometry relaxation-induced large Stokes shift.

Ma Jie J Zhang Yizhi Y Zhang Hongbo H He Xifeng X

RSC advances 20200930 59

The dyes (P-1 and P-2) of perylenebisimide (PBI) conjugated with 2-(2-hydroxyphenyl)benzothiazole (HBT) were prepared by Sonogashira coupling reaction. The new compounds have special photophysical properties, such as near infrared absorption/emission and large Stokes shift. The UV-vis absorption (range from 651 nm to 690 nm) and emission wavelength (range from 732 nm to 756 nm) of P-1 and P-2 extend to near infrared range. Importantly, they have much larger Stokes shifts (range from 73 nm to 105 ...[more]

PMID: 35517115

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