Preparation and Optical Waveguide Property of Benzothiadiazole-Containing One Dimensional Micro-nanowires

doi:10.19894/j.issn.1000-0518.210071

Chinese Journal of Applied Chemistry ›› 2021, Vol. 38 ›› Issue (11): 1479-1485.DOI: 10.19894/j.issn.1000-0518.210071

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Preparation and Optical Waveguide Property of Benzothiadiazole-Containing One Dimensional Micro-nanowires

CHEN Song-Hua¹, CHEN Xin², LIU Yong-Qi¹, HE Mei-Yun¹, FU Shan-Shan¹, PENG Li¹, YANG Ji-En^3*

¹College of Chemistry and Material, Longyan University, Longyan 364000, China;
²National Science Library, Chinese Academy of Sciences, Beijing 100190, China;
³School of Materials Science and Engineering, Henan Normal University, Xinxiang 453007, China

Received:2021-02-18 Accepted:2021-06-11 Published:2021-11-01 Online:2022-01-01
Supported by:
Research Funds of Longyan University (No.LB2018016), the Youth Talented Scholars Plan in Universities of Fujian Province, Young and Middle-aged Teacher in Science Research of Fujian Province (No.JAT190732) and the Science and Technology Program of Henan (No.192102210173)

Abstract

Abstract: This study describes the synthesis of 1,4-disubstitued-1,2,3-triazole benzothiadiazole derivatives (4,7-bis(1-phenyl-1H-1,2,3-triazol-4-yl)benzo[c][1,2,5]thiadiazole, BT-DC) through Cu(Ⅰ)-catalyzed “Click” reaction. The well-defined one-dimensional micro-nanowires in large quantities and with high morphological purity are successfully fabricated using a liquid phase assembly method. The length of one-dimensional microwires is more than 100 μm with the width of 500 nm~2 μm. Meanwhile, these assembles show a typical characteristic of the waveguiding behavior. Scanning near-field optical microscopy finds that the fluorescence from the BT-DC excited with an ultraviolet laser is effectively confined in the microwire structure and propagates along the one-dimensional direction. The optical loss coefficient of BT-DC is 0.61 dB/μm at 351 nm, endowing potential applications in the field of optical devices.

Key words: Benzothiadiazole, Self-assembly, Micro-nanowires, Optical waveguide

CLC Number:

O621.2

CHEN Song-Hua, CHEN Xin, LIU Yong-Qi, HE Mei-Yun, FU Shan-Shan, PENG Li, YANG Ji-En. Preparation and Optical Waveguide Property of Benzothiadiazole-Containing One Dimensional Micro-nanowires[J]. Chinese Journal of Applied Chemistry, 2021, 38(11): 1479-1485.

References

[1] DAS G, BISWAL B P, KANDAMBETH S, et al. Chemical sensing in two dimensional porous covalent organic nanosheets[J]. Chem Sci, 2015, 6(7): 3931-3939.
[2] MENG D, FU T, XIAO C Y, et al. Three-bladed rylene propellers with three-dimensional network assembly for organic electronics[J]. J Am Chem Soc, 2016, 138(32): 10184-10190.
[3] PENG Y W, HUANG Y, ZHU Y H, et al. Ultrathin two-dimensional covalent organic framework nanosheets: preparation and application in highly sensitive and selective dna detection[J]. J Am Chem Soc, 2017, 139(25): 8698-8704.
[4] CHEN N, LIU Q W, LIU C, et al. MEG actualized by high-valent metal carrier transport[J]. Nano Energy, 2019, 65: 104047.
[5] CHEN N, XIAO T H, LUO Z Y, et al. Porous carbon nanowire array for surface-enhanced Raman spectroscopy[J]. Nat Commun, 2020, 11(1): 4772.
[6] 孙小彤, 陈南,梁含雪, 等. 阳极氧化铝模板限域制备一维杂化纳米材料及其多样化应用的研究进展[J]. 应用化学, 2020, 37(2): 123-133.
SUN X T, CHEN N, LIANG H X, et al.Progress of fabrication of one-dimensional hybrid nanomaterials by template-confined growth and their diverse applications[J]. Chinese J Appl Chem, 2020, 37(2): 123-133.
[7] ZHANG W, YAN Y L, GU J M, et al. Low-threshold wavelength-switchable organic nanowire lasers based on excited-state intramolecular proton transfer[J]. Angew Chem Int Ed, 2015, 54(24): 7125-7129.
[8] ZHENG H Y, LI Y J, LIU H B, et al. Construction of heterostructure materials toward functionality[J]. Chem Soc Rev, 2011, 40(9): 4506-4524.
[9] LI Y J, LIU T F, LIU H B, et al. Self-assembly of intramolecular charge-transfer compounds into functional molecular systems[J]. Acc Chem Res, 2014, 47(4): 1186-1198.
[10] LIU H B, XU J L, LI Y J, et al. Aggregate nanostructures of organic molecular materials[J]. Acc Chem Res, 2010, 43(12): 1496-1508.
[11] ZHAO Y S, XU J J, PENG A D, et al. Optical waveguide based on crystalline organic microtubes and microrods[J]. Angew Chem Int Ed, 2008, 47(38): 7301-7305.
[12] YAO W, YAN Y L, XUE L, et al. Controlling the structures and photonic properties of organic nanomaterials by molecular design[J]. Angew Chem Int Ed, 2013, 52(33): 8713-8717.
[13] SHIROTA Y. Organic materials for electronic and optoelectronic devices[J]. J Mater Chem, 2000, 10(1): 1-25.
[14] XU J L, SEMIN S, NIEDZIALEK D, et al. Self-assembled organic microfibers for nonlinear optics[J]. Adv Mater, 2013, 25(14): 2084-2089.
[15] CHEN S H, CHEN N, YAN Y L, et al. Controlling growth of molecular crystal aggregates for efficient optical waveguides[J]. Chem Commun, 2012, 48(72): 9011-9013.
[16] CHEN S H, LI Y J, LI Y L. Architecture of low dimensional nanostructures based on conjugated polymers[J]. Polym Chem, 2013, 4(20): 5162-5180.
[17] DU J, BIEWER M C, STEFAN M C. Benzothiadiazole building units in solution-processable small molecules for organic photovoltaics[J]. J Mater Chem A, 2016, 4(41): 15771-15787.
[18] 王丽辉, 殷伦祥, 张昱, 等. 苯并噻二唑为中心的A-π-A-π-A型小分子光伏材料合成与性能研究[J]. 大连理工大学学报, 2014, 54(2): 163-170.
WANG L H, YIN L X, ZHANG Y, et al. Reasearch of synthesis and properties of benzothiadiazole-based A-π-A-π-A-type small-molecule photovoltaic materials[J]. J Dalian Univ Tech, 2014, 54(2): 163-170.
[19] NI F, WU Z B, ZHU Z C, et al. Teaching an old acceptor new tricks: rationally employing 2,1,3-benzothiadiazole as input to design a highly efficient red thermally activated delayed fluorescence emitter[J]. J Mater Chem C, 2017, 5(6): 1363-1368.
[20] ZHAO Z Y, YIN Z H, CHEN H J, et al. High-performance, air-stable field-effect transistors based on heteroatom-substituted naphthalenediimide-benzothiadiazole copolymers exhibiting ultrahigh electron mobility up to 8.5 cm V^-1 s^-1[J]. Adv Mater, 2017, 29(4): 1602410.
[21] 陈松华, 陈欣, 刘永琦, 等. 以咔唑为给体的分子内电荷转移化合物的自组装及发光性质研究[J]. 应用化学, 2010, 37(9): 1022-1029.
CHEN S H, CHEN X, LIU Y Q, et al. Self-assembly and luminescence properties of intramolecular charge transfer compound of carbazole derivative[J]. Chinese J Appl Chem, 2020, 37(9): 1022-1029.
[22] HE B Z, SU H F, BAI T W, et al. Spontaneous amino-yne click polymerization: a powerful tool toward regio- and stereospecific poly(beta-aminoacrylate)s[J]. J Am Chem Soc, 2017, 139(15): 5437-5443.
[23] LI Y W, DONG X H, ZOU Y, et al. Polyhedral oligomeric silsesquioxane meets “click” chemistry: rational design and facile preparation of functional hybrid materials[J]. Polymer, 2017, 125: 303-329.
[24] LEWIS W G, GREEN L G, GRYNSZPAN F, et al. Click chemistry in situ: acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks[J]. Angew Chem Int Ed, 2002, 41(6): 1053-1057.
[25] LI Y J, FLOOD A H. Strong, size-selective, and electronically tunable C—H… halide binding with steric control over aggregation from synthetically modular, shape-persistent [3₄]triazolophanes[J]. J Am Chem Soc, 2008, 130(36): 12111-12122.
[26] HUANG X B, MENG J, DONG Y, et al. Polymer-based fluorescence sensors incorporating chiral binaphthyl and benzo [2,1,3]thiadiazole moieties for Hg²⁺ detection[J]. J Polym Sci Pol Chem, 2010, 48(5): 997-1006.
[27] NETO B A D, LAPIS A A M, DASILVA E N, et al. 2,1,3-Benzothiadiazole and derivatives: synthesis, properties, reactions, and applications in light technology of small molecules[J]. Eur J Org Chem 2013, 2013(2): 228-255.
[28] ZHAO N, LI M, YAN Y L, et al. A tetraphenylethene-substituted pyridinium salt with multiple functionalities: synthesis, stimuli-responsive emission, optical waveguide and specific mitochondrion imaging[J]. J Mater Chem C, 2013, 1(31): 4640-4646.
[29] LI Y, MA Z Y, LI A, et al. A single crystal with multiple functions of optical waveguide, aggregation-induced emission, and mechanochromism[J]. ACS Appl Mater Interfaces, 2017, 9(10): 8910-8918.
[30] 白若男, 李青, 乔山林, 等. 1,4-二咔唑基苯微米结构的可控制备及光波导性质[J]. 高等学校化学学报, 2020, 41(5): 967-971.
BAI R N, LI Q, QIAO S L, et al. Controlled preparation and optical waveguide property of 1,4-dicarbazolidinylbenzene microwires[J]. Chem J Chinese Univ, 2020,41(5):967-971.
[31] LI Q, JIN W, CHU M M, et al. Tailoring the structures and photonic properties of low-dimensional organic materials by crystal engineering[J]. Nanoscale, 2018, 10(10): 4680-4685.

Preparation and Optical Waveguide Property of Benzothiadiazole-Containing One Dimensional Micro-nanowires

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