Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

Guangqian Ji; Nan Wang; Xiaodong Yin; Pangkuan Chen

doi:10.1021/acs.orglett.0c01777

Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

Guangqian Ji, Nan Wang, Xiaodong Yin, Pangkuan Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

19 Citations (Scopus)

Abstract

We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of substituents on N leads to stronger emission responses upon trans-to-cis photoisomerization. Upon further approach, a bistable isomer was photochemically achieved (4: R1 = Me, R2 = H) with quenched emission, which is ascribed to the pronounced B···N constraint via B ← NH coordination in cis-4.

Original language	English
Pages (from-to)	5758-5762
Number of pages	5
Journal	Organic Letters
Volume	22
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.0c01777
Publication status	Published - 7 Aug 2020

Access to Document

10.1021/acs.orglett.0c01777

Cite this

@article{b367bbffd3da4a028d235f2928248219,

title = "Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints",

abstract = "We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of substituents on N leads to stronger emission responses upon trans-to-cis photoisomerization. Upon further approach, a bistable isomer was photochemically achieved (4: R1 = Me, R2 = H) with quenched emission, which is ascribed to the pronounced B···N constraint via B ← NH coordination in cis-4.",

author = "Guangqian Ji and Nan Wang and Xiaodong Yin and Pangkuan Chen",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = aug,

day = "7",

doi = "10.1021/acs.orglett.0c01777",

language = "English",

volume = "22",

pages = "5758--5762",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

AU - Ji, Guangqian

AU - Wang, Nan

AU - Yin, Xiaodong

AU - Chen, Pangkuan

PY - 2020/8/7

Y1 - 2020/8/7

N2 - We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of substituents on N leads to stronger emission responses upon trans-to-cis photoisomerization. Upon further approach, a bistable isomer was photochemically achieved (4: R1 = Me, R2 = H) with quenched emission, which is ascribed to the pronounced B···N constraint via B ← NH coordination in cis-4.

AB - We present a family of stilbene derivatives (1-4) ortho-functionalized with an electron donor and acceptor. Their emission was tuned by donor substitutions, dictating charge transfer dependent on the N···B spatial separation. The steric reduction of substituents on N leads to stronger emission responses upon trans-to-cis photoisomerization. Upon further approach, a bistable isomer was photochemically achieved (4: R1 = Me, R2 = H) with quenched emission, which is ascribed to the pronounced B···N constraint via B ← NH coordination in cis-4.

UR - http://www.scopus.com/inward/record.url?scp=85088568247&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.0c01777

DO - 10.1021/acs.orglett.0c01777

M3 - Article

C2 - 32645271

AN - SCOPUS:85088568247

SN - 1523-7060

VL - 22

SP - 5758

EP - 5762

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Substituent Effect Induces Emission Modulation of Stilbene Photoswitches by Spatial Tuning of the N/B Electronic Constraints

Abstract

Access to Document

Other files and links

Fingerprint

Cite this