Helicene‐type β‐isoindigo‐based boron‐dipyrromethene analogs with strong near‐infrared chiroptical activity
Ziwei Chen,
Zhigang Ni,
Xing‐Yu Chen,
Yongqiang Xu,
Chunyan Yu,
SiSi Wang,
Xiao‐Ye Wang,
Hua Lu
Affiliations
Ziwei Chen
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
Zhigang Ni
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
Xing‐Yu Chen
State Key Laboratory of Elemento‐Organic Chemistry Frontiers Science Center for New Organic Matter College of Chemistry Nankai University Tianjin China
Yongqiang Xu
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
Chunyan Yu
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
SiSi Wang
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
Xiao‐Ye Wang
State Key Laboratory of Elemento‐Organic Chemistry Frontiers Science Center for New Organic Matter College of Chemistry Nankai University Tianjin China
Hua Lu
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education and Key Laboratory of Organosilicon Material Technology of Zhejiang Province College of Material Chemistry and Chemical Engineering Hangzhou Normal University Hangzhou China
Abstract Near‐infrared (NIR) chiroptical response has been less explored because it is challenging to achieve both chirality and NIR absorption/emission. Herein, we describe the design of heterohelicene‐type β‐isoindigo‐based boron‐dipyrromethene (BODIPY) analogs (β‐IBs), which shift the absorption peak to 800 nm and produce significant Cotton effects (127.8 M−1 cm−1) and absorbance dissymmetry factors (|gabs| = 3.5 × 10−3). The luminescence dissymmetry factor (glum) and circularly polarized luminescence (CPL) brightness (BCPL) of up to 1.24 × 10−3 and 1.78 M−1 cm−1 were realized beyond 800 nm. These β‐IBs are the first examples of helicene‐type compounds with the highest gabs in the NIR region and CPL beyond 800 nm. Theoretical calculations demonstrate that the strong chiroptical activities are triggered by their large transition magnetic dipole moments. This study not only provides a new approach to the synthesis of a larger variety of unprecedented helicene‐type BODIPY analogs but also demonstrates excellent NIR chiroptical properties.
