Citation: Shimin Zhou, Yang Liu, Yuyin Hao, Zhiqiang Liu, Xiaoqiang Yu. Dimesitylboryl-ended oligothiophene with tetrazine as core: Synthesis, structure and Diels–Alder reactivity[J]. Chinese Chemical Letters, ;2024, 35(1): 108325. doi: 10.1016/j.cclet.2023.108325 shu

Dimesitylboryl-ended oligothiophene with tetrazine as core: Synthesis, structure and Diels–Alder reactivity

Shimin Zhou ^{a, b} ,
Yang Liu ^{a, b} ,
Yuyin Hao ^{a, b} ,
Zhiqiang Liu ^{a, b, *,} ,
Xiaoqiang Yu ^{a, *,}

a.
State Key Laboratory of Crystal Materials, Shandong University, Ji'nan 250100, China
b.
Shenzhen Research Institute of Shandong University, Shenzhen 518057, China

zqliu@sdu.edu.cn

yuxq@sdu.edu.cn

Received Date: 31 December 2022
Revised Date: 2 March 2023
Accepted Date: 8 March 2023
Available Online: 12 March 2023

Figures(6)

A dimesitylboryl-ended oligothiophene with tetrazine as core (BTz) was synthesized and its reactivity and spectral changes toward trans-cyclooctene ((4E)-TCO-OH), cis-cyclooctene and bicyclo[6.1.0]non-4-yn-9-ylmethanol were comprehensively studied. The fluorescence intensity of BTz was enhanced up to more than 100 times upon bioorthogonal reaction with (4E)-TCO-OH. In addition, the first crystal structure of isolated product of tetrazine derivative with cyclooctene was determined, which clearly confirmed a dehydrogenation occurred after Diels–Alder reaction under ambient conditions.
- Tetrazine ligation,
- Bioorthogonal reaction,
- Crystal structure,
- Fluorescence,
- Quadrupolar hybrid-oligothiophene
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