Donor-Acceptor Type Chiral Tetracoordinate Organoboranes and Their Optical Properties

doi:10.19894/j.issn.1000-0518.220398

Chinese Journal of Applied Chemistry ›› 2023, Vol. 40 ›› Issue (5): 743-748.DOI: 10.19894/j.issn.1000-0518.220398

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Donor-Acceptor Type Chiral Tetracoordinate Organoboranes and Their Optical Properties

Yue YANG¹, Shi-Wen HUANG¹, Yue TONG¹, Ze-Da CHEN¹, Ben-Hua MA¹(), Chuan-Dong DOU¹^,²()

^1.State Key Laboratory of Supramolecular Structure and Materials，College of Chemistry，Jinlin University，Changchun 130022，China
^2.Jiangsu Engineering Laboratory of Novel Functional Polymeric Materials，Soochow University，Suzhou 215123，China

Received:2022-12-12 Accepted:2023-03-07 Published:2023-05-01 Online:2023-05-26
Contact: Ben-Hua MA,Chuan-Dong DOU
About author:mabh@jlu.edu.cn
chuandong@jlu.edu.cn
Supported by:
Jilin Scientific and Technological Development Program(20220101054JC);the National Natural Science Foundation of China(22175074)

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Abstract

Abstract:

Circularly polarized luminescence （CPL） organic molecules， an important class of chiral optical materials， have received great attention in the fields of organic optics and organic electronics. In this study， we simultaneously incorporate chiral binaphthyl moieties into and construct donor-acceptor electronic structures of double B←N bridged bipyridine. We synthesize a series of chiral tetracoordinate organoborane molecules with donor-acceptor electronic structures. While the molecules containing the diphenylamine and carbazole units exhibit conventional aggregation-caused quenching emission phenomenon， the compound bearing with the 9，9-dimethyl-9，10-dihydroacridine group has unique aggregation-induced emission property. More importantly， incorporation of two axially chiral binaphthyl moieties makes them possess intriguing chiral optical properties， as proved by circular dichroism and CPL measurements. The luminescence dissymmetric factors of their CPL properties are exceeding 1×10^-3.

Key words: Organoborane, Donor-acceptor structure, Chiral, Circularly polarized luminescence, Aggregation-induced emission

CLC Number:

O626.5

Yue YANG, Shi-Wen HUANG, Yue TONG, Ze-Da CHEN, Ben-Hua MA, Chuan-Dong DOU. Donor-Acceptor Type Chiral Tetracoordinate Organoboranes and Their Optical Properties[J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 743-748.

Figures/Tables 3

Fig.1 （A） Synthesis of 2a， 2b and 2c；（B） X-ray single-crystal structure of 2a

Fig.2 （A） UV-Vis absorption and fluorescence spectra of toluene solutions and thin films of 2a， 2b and 2c； Fluorescence spectra of （B） 2a，（C） 2b and （D） 2c in THF/water mixtures with different water volume fractions. Insets are photographs of the solutions under UV light （365 nm）

Fig.3 （A） Circular dichroism and circularly polarized luminescence spectra of 2a， 2b and 2c；（B） Cyclic voltammograms of 2a， 2b and 2c in CH2Cl2 for oxidation and in THF for reduction using n-Bu4NPF6 as the electrolyte

References 30

1	SCHADT M. Liquid crystal materials and liquid crystal displays［J］. Annu Rev Mater Sci， 1997， 27： 305-379.
2	OKUTANI K， NOZAKI K， IWAMURA M. Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis（diimine）dicarboxylic acid europium（III） complexes［J］. Inorg Chem， 2014， 53： 5527-5537.
3	YANG S， WANG Y， PENG C， et al. Circularly polarized thermally activated delayed fluorescence emitters in through-space charge transfer on asymmetric spiro skeletons［J］. J Am Chem Soc， 2020， 142（41）： 17756-17765.
4	ZINNA F， BARI L. Lanthanide circularly polarized luminescence： bases and applications［J］. Chirality， 2015， 27： 1-13.
5	赵常利，秦明高，窦晓秋，等. 纳米颗粒增强的手性超分子水凝胶成骨性能［J］. 应用化学， 2022， 39（1）： 177-187.
	ZHAO C L， QIN M G， DOU X Q， et al. High mechanical stability and osteogenesis of chiral supramolecular hydrogel induced by inorganic nanoparticles［J］. Chin J Appl Chem， 2022， 39（1）： 177-187.
6	MAEDA C， NAGAHATA K， SHIRAKAWA T， et al. Azahelicene-fused BODIPY analogues showing circularly polarized luminescence［J］. Angew Chem Int Ed， 2020， 59： 7813-7817.
7	LIU Q， XIA Q， WANG S， et al. In situ visualizable self-assembly， aggregation-induced emission and circularly polarized luminescence of tetraphenylethene and alanine-based chiral polytriazole［J］. J Mater Chem C， 2018， 6： 4807-4816.
8	DHBAIBI K， FAVEREAU L， SREBRO-HOOPER M. Exciton coupling in diketopyrrolopyrrole-helicene derivatives leads to red and near-infrared circularly polarized luminescence［J］. Chem Sci， 2018， 9： 735-742.
9	XU Q， WANG C， HE J， et al. Corannulene-based nanographene containing helical motifs［J］. Org Chem Front， 2021， 8： 2970-2976.
10	刘传涛，肖婷，王芳，等. 一种基于联萘衍生物荧光探针的合成及其对精氨酸的识别［J］. 应用化学， 2018， 35（1）： 40-45.
	LIU C T， XIAO T， WANG F， et al. Synthesis of binol based fluorescence probe and recognition of arginine［J］. Chin J Appl Chem， 2018， 35（1）： 40-45.
11	JIMÉNEZ J， MORENO F， ARBELOA T， et al. Isopinocampheyl-based C-BODIPYs： a model strategy to construct cost-effective boron-chelate emitters of circularly polarized light［J］. Org Chem Front， 2021， 8： 4752-4757.
12	HIRAI M， TANAKA N， SAKAI M， et al. Structurally constrained boron-， nitrogen-， silicon-， and phosphorus-centered polycyclic π-conjugated systems［J］. Chem Rev， 2019， 119： 8291-331.
13	GROTTHUSS E， JOHN A， KAESE T， et al. Doping polycyclic aromatics with boron for superior performance in materials science and catalysis［J］. Asian J Org Chem， 2018， 7： 37-53.
14	JÄKLE F. Advances in the synthesis of organoborane polymers for optical， electronic， and sensory applications［J］. Chem Rev， 2010， 110： 3985-4022.
15	GUO J， YNAG Y， DOU C， et al. Boron-containing organic diradicaloids： dynamically modulating singlet diradical character by Lewis acid-base coordination［J］. J Am Chem Soc， 2021， 143（43）： 18272-18279.
16	YUAN L， GUO J， YANG Y， et al. A C₅₄B₂ polycyclic π-system with bilayer assembly and multi-redox activity［J］. CCS Chem， 2022， 5： 876-884.
17	MELLERUP S， WANG S. Boron-doped molecules for optoelectronics［J］. Trends Chem， 2019， 1： 77-89.
18	RAY C， SÁNCHEZ-CARNERERO E M， MORENO F， et al. Bis（haloBODIPYs） with labile helicity： valuable simple organic molecules that enable circularly polarized luminescence［J］. Chem Eur J， 2016， 22： 8805-8808.
19	WANG J Y， PEI J. BN-embedded aromatics for optoelectronic applications［J］. Chin Chem Lett， 2016， 27： 1139-1146.
20	YANG W， LI N， MIAO J， et al. Simple double hetero［5］helicenes realize highly efficient and narrowband circularly polarized organic light-emitting diodes［J］. CCS Chem， 2022， 4： 3463-3471.
21	DOU C， LONG X， DING Z， et al. An electron-deficient building block based on the B←N unit： an electron acceptor for all-polymer solar cells［J］. Angew Chem Int Ed， 2016， 55（4）： 1436-1440.
22	DOU C， LIU J， WANG L. Conjugated polymers containing B←N unit as electron acceptors for all-polymer solar cells［J］. Sci China Chem， 2017， 60： 450-459.
23	ZHAO R， LIU J， WANG L. Polymer acceptors containing B←N units for organic photovoltaics［J］. Acc Chem Res， 2020， 53： 1557-67.
24	YANG Y， YUAN L， GUO J， et al. Organoborane emitter containing double B←N bridged bipyridine that displays delayed fluorescence and aggregation-induced emission［J］. Dyes Pigm， 2022， 207： 1-6.
25	YANG Y， GUO J， YE K， et al. Chiral tetracoordinate organoboranes based on double B←N bridged bipyridine with circularly polarized luminescence［J］. Mater Chem Front， 2022， 6： 600-606.
26	BIRKS J. Photophysics of aromatic molecules［M］. London： Wileyinterscience， 1970.
27	MEI J， HONG Y， LAM J， et al. Aggregation-induced emission： the whole is more brilliant than the parts［J］. Adv Mater， 2014， 26： 5429-5479.
28	MASON S. Molecular optical activity and chiral discriminations［M］. Cambridge： Cambridge University Press， 1982， Chapter 1-2.
29	JIMÉNEZ J， DÍAZ-NORAMBUENA C， SERRANO S， et al. BINOLated aminostyryl BODIPYs： a workable organic molecular platform for NIR circularly polarized luminescence［J］. Chem Commun， 2021， 57： 5750-5753.
30	DOMÍNGUEZ Z， LÓPEZ-RODRÍGUEZ R， ÁLVAREZ E， et al. Azabora［5］helicene charge-transfer dyes show efficient and spectrally variable circularly polarized luminescence［J］. Chem Eur J， 2018， 24： 12660-12668.

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Donor-Acceptor Type Chiral Tetracoordinate Organoboranes and Their Optical Properties

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