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Chemical Tongues and Noses Based upon Conjugated Polymers

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Abstract

We report the uses of conjugated polymers in multisensory applications and in chemical and optoelectronic tongues. We look at the potential of single polymers to discriminate multiple analytes and into small libraries of conjugated polymers that represent sensors. These small libraries combine several barely selective, promiscuous sensor elements and react with the analytes in a fairly non-selective fashion by change of color, emission wavelength, or emission intensity. In such optoelectronic noses and tongues, response of a single element is not specific or particularly useful at all, but the response pattern after the combination of several sensor elements is often specific for an analyte and allows discrimination and identification without any problem. These types of tongues and noses are well suited for quality control of foodstuff, beverages, and biological species such as proteins or cells. The discriminative process is often not well understood but it is powerful, particularly if the obtained data are analyzed by sophisticated statistical methods, i.e., linear discriminant analysis and/or principal component analysis. This added layer of analysis extracts the hidden information/patterns out of the data and allows visualization of the results.

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Fig. 1

Reprinted with permission from Han J, Wang B, Bender M, Kushida S, Seehafer K, Bunz UHF (2017) ACS Appl Mater Interfaces 9(1):790–797. Copyright 2017 American Chemical Society

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Fig. 3

b, c Reprinted with permission from Wang F, Liu Z, Wang B, Feng L, Liu L, Lv F, Wang Y, Wang S (2014) Angew. Chem. Int. Ed. 53(2):424–428. Copyright 2014 John Wiley and Sons

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Fig. 6

b–d Reprinted with permission from Wu Y, Tan Y, Wu J, Chen S, Chen YZ, Zhou X, Jiang Y, Tan C (2015) ACS Appl Mater Interfaces 7(12):6882–6888. Copyright 2015 American Chemical Society

Fig. 7

b Adapted with permission from Xu H, Wu W, Chen Y, Qiu T, Fan L-J (2014) ACS Appl Mater Interfaces 6(7):5041–5049. Copyright 2014 American Chemical Society

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Fig. 9

b Reprinted with permission from Miranda OR, You C–C, Phillips R, Kim I-B, Ghosh PS, Bunz UHF, Rotello VM (2007) J. Am. Chem. Soc. 129(32):9856–9857. Copyright 2007 American Chemical Society

Fig. 10
Fig. 11

b Reprinted with permission from Wu D, Schanze KS (2014) Appl. Mater. Interfaces 6(10):7643–7651. Copyright 2014 American Chemical Society

Fig. 12

b, c Adapted with permission from Dou WT, Zeng YL, Lv Y, Wu J, He XP, Chen GR, Tan C (2016) ACS Appl Mater Inter 8(21):13601–13606. Copyright 2016 American Chemical Society

Fig. 13

b, c Reprinted from Biosensors and Bioelectronics, 26, Niamnont N, Mungkarndee R, Techakriengkrai I, Rashatasakhon P, Sukwattanasinitt M, Protein discrimination by fluorescent sensor array constituted of variously charged dendritic phenylene–ethynylene fluorophores, 863–867, Copyright (2010), with permission from Elsevier

Fig. 14

b, c adapted with permission from Sun P, Lu X, Fan Q, Zhang Z, Song W, Li B, Huang L, Peng J, Huang W (2011) Macromolecules 44:8763–8770. Copyright 2011 American Chemical Society

Fig. 15

b, c Reproduced from Ref. [45] with permission from the Royal Society of Chemistry

Fig. 16

a Reprinted with permission from Pun CC, Lee K, Kim HJ, Kim J (2006) Macromolecules 39:7461–7463. Copyright 2006 American Chemical Society

Fig. 17

Reprinted by permission from Macmillan Publishers Ltd: Nature Communication 48, 2012

Fig. 18

Reprinted from Sens Actuators B, 222, Golabi M, Turner APF, Jager EWH, Tunable conjugated polymers for bacterial differentiation, 839–848, Copyright (2016), with permission from Elsevier

Fig. 19

b–e Reproduced from Ref. [51] with permission from the Royal Society of Chemistry

Fig. 20

b–d Reprinted with permission from Satrijo A, Swager TM (2007) J Am Chem Soc 129:16020–16028. Copyright 2007 American Chemical Society

Fig. 21

b Reprinted with permission from Maynor MS, Nelson TL, O’Sulliva C, Lavigne JJ (2007) Org Lett 9(17):3217–3220. Copyright 2007 American Chemical Society

Fig. 22

Reprinted with permission from Maynor MS, Nelson TL, O’Sulliva C, Lavigne JJ (2007) Org Lett 9(17):3217–3220. Copyright 2007 American Chemical Society

Fig. 23

b, c Reproduced from Ref. [54] with permission from the Royal Society of Chemistry

Fig. 24

b, c Reprinted with permission from Rochat S, Swager TM, Fluorescence sensing of amine vapors using a cationic conjugated polymer combined with various anions (2014) Angew Chem Int Ed 53(37):9792–9796. Copyright 2014 John Wiley and Sons

Fig. 25

Reprinted from Syn Met, 161, He C, He Q, Deng C, Shi L, Fu Y, Cao H, Cheng J, Determination of methamphetamine hydrochloride by highly fluorescent polyfluorene with NH2-terminated side chains, 293–297, Copyright (2011), with permission from Elsevier

Fig. 26

a, b Adapted with permission from Kimura M, Sakai R, Sato S, Fukawa T, Ikehara T, Maeda R, Mihara T (2012) Adv Funct Mater 22: 469–476. Copyright 2012 John Wiley and Sons

Fig. 27
Fig. 28

b, c Adapted with permission from Borzin E, Shemesh A, Hertzog-Ronen C, Gerchikov Y, Tessler N, Eichen Y (2010) Journal of Physical Organic Chemistry 23, 1108–1113. Copyright 2010 John Wiley and Sons

Fig. 29

Reprinted with permission from Liao HC, Hsu CP, Wu MC, Lu CF, Su WF (2013) Anal. Chem. 85 (19), 9305–9311. Copyright 2013 American Chemical Society

Fig. 30

c, d Reprinted from Sens. Actuators, B, 142, Gonçalves VC, Balogh DT, Optical VOCs detection using poly(3-alkylthiophenes) with different side-chain lengths, 55–60. Copyright (2009), with permission from Elsevier

Fig. 31

a, c Reprinted from Anal. Chim. Acta, 597, Si P, Mortensen J, Komolov A, Denborg J, Polymer coated quartz crystal microbalance sensors for detection of volatile organic compounds in gas mixtures, 223–230, Copyright (2007), with permission from Elsevier

Fig. 32

Reprinted with permission from Han J, Wang B, Bender M, Seehafer K, Bunz UHF (2016) ACS Appl. Mater. Interfaces 8, 20415–20421. Copyright 2016 American Chemical Society

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Fig. 34

a, b Reproduced from Ref. [66] with permission from the Royal Society of Chemistry

Fig. 35

Reproduced from Ref. [67] with permission from the Royal Society of Chemistry

Fig. 36

Science China Chemistry Conjugated polyelectrolytes for label-free visual detection of heparin, 54, 2011, 567–574, Pu K, Zhan R, Liang J, Liu B. Reproduced with permission of Springer

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Authors and Affiliations

  1. Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Jan Freudenberg, Felix Hinkel, Daniel Jänsch & Uwe H. F. Bunz

  2. Centre for Advanced Materials (CAM), Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany

    Felix Hinkel & Uwe H. F. Bunz

  3. InnovationLab GmbH, Speyerer Straße 4, 69120, Heidelberg, Germany

    Jan Freudenberg & Daniel Jänsch

Authors
  1. Jan Freudenberg
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  2. Felix Hinkel
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  3. Daniel Jänsch
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  4. Uwe H. F. Bunz
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Corresponding author

Correspondence to Uwe H. F. Bunz.

Additional information

This article is part of the Topical Collection “Polymer Synthesis Based on Triple-Bond Building Blocks”, edited by Ben Zhong Tang and Rongrong Hu.

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Freudenberg, J., Hinkel, F., Jänsch, D. et al. Chemical Tongues and Noses Based upon Conjugated Polymers. Top Curr Chem (Z) 375, 67 (2017). https://doi.org/10.1007/s41061-017-0155-2

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