Skip to main content
SpringerLink
Log in

Chemical Tongues and Noses Based upon Conjugated Polymers

  • Review
  • Published:
Topics in Current Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

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

Fig. 2
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

Fig. 4
Fig. 5
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

Fig. 8
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

Fig. 33
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

Similar content being viewed by others

References

  1. Metzger A, Anslyn EV (1998) Angew Chem Int Ed 37(5):649–652

    Article  CAS  Google Scholar 

  2. Wiskur SL, Anslyn EV (2001) J Am Chem Soc 123(41):10109–10110

    Article  CAS  Google Scholar 

  3. Rakow NA, Suslick KS (2000) Nature 406(6797):710–713

    Article  CAS  Google Scholar 

  4. Zhang C, Suslick KS (2007) J Agric Food Chem 55(2):237–242

    Article  CAS  Google Scholar 

  5. Rana S, Singla AK, Bajaj A, Elci SG, Miranda OR, Mout R, Yan B, Jirik FR, Rotello VM (2012) ACS Nano 6(9):8233–8240

    Article  CAS  Google Scholar 

  6. Peveler WJ, Yazdani M, Rotello VM (2016) ACS Sens 1(11):1282–1285

    Article  CAS  Google Scholar 

  7. You C-C, Miranda OR, Gider B, Ghosh PS, Kim I-B, Erdogan B, Krovi SA, Bunz UHF, Rotello VM (2007) Nat Nanotech 2(5):318–323

    Article  CAS  Google Scholar 

  8. Bunz UHF, Rotello VM (2010) Angew Chem Int Ed 49(19):3268–3279

    Article  CAS  Google Scholar 

  9. Askim JR, Mahmoudi M, Suslick KS (2013) Chem Soc Rev 42(22):8649–8682

    Article  CAS  Google Scholar 

  10. Musto CJ, Suslick KS (2010) Curr Opin Chem Biol 14(6):758–766

    Article  CAS  Google Scholar 

  11. Wiskur SL, Ait-Haddou H, Lavigne JJ, Anslyn EV (2001) Acc Chem Res 34(12):963–972

    Article  CAS  Google Scholar 

  12. Lavigne JJ, Anslyn EV (2001) Angew Chem Int Ed 40(17):3118–3130

    Article  CAS  Google Scholar 

  13. Anslyn EV (2007) J Org Chem 72(3):687–699

    Article  CAS  Google Scholar 

  14. Hargrove AE, Nieto S, Zhang T, Sessler JL, Anslyn EV (2011) Chem Rev 111(11):6603–6782

    Article  CAS  Google Scholar 

  15. Wu J, Kwon B, Liu W, Anslyn EV, Wang P, Kim JS (2015) Chem Rev 115(15):7893–7943

    Article  CAS  Google Scholar 

  16. Stewart S, Ivy MA, Anslyn EV (2014) Chem Soc Rev 43(1):70–84

    Article  CAS  Google Scholar 

  17. Baldwin EA, Bai J, Plotto A, Dea S (2011) Sensors 11(5):4744–4766

    Article  Google Scholar 

  18. Han J, Wang B, Bender M, Kushida S, Seehafer K, Bunz UHF (2017) ACS Appl Mater Interfaces 9(1):790–797

    Article  CAS  Google Scholar 

  19. Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Chem Rev 109(3):897–1091

    Article  CAS  Google Scholar 

  20. Cheng Y-J, Yang S-H, Hsu C-S (2009) Chem Rev 109(11):5868–5923

    Article  CAS  Google Scholar 

  21. Grazulevicius JV, Strohriegl P, Pielichowski J, Pielichowski K (2003) Prog Polym Sci 28(9):1297–1353

    Article  CAS  Google Scholar 

  22. Bunz UHF (2000) Chem Rev 100(4):1605–1644

    Article  CAS  Google Scholar 

  23. Bunz UHF (2009) Macromol Rap Commun 30(9–10):772–805

    Article  CAS  Google Scholar 

  24. Scherf U, List E (2002) Adv Mater 14(7):477–487

    Article  CAS  Google Scholar 

  25. Leclerc M (2001) J Polym Sci A Polym Chem 39(17):2867–2873

    Article  CAS  Google Scholar 

  26. Perepichka IF, Perepichka DF, Meng H, Wudl F (2005) Adv Mater 17(19):2281–2305

    Article  CAS  Google Scholar 

  27. Roncali J (1992) Chem Rev 92(4):711–738

    Article  CAS  Google Scholar 

  28. McCullough RD (1998) Adv Mater 10(2):93–116

    Article  CAS  Google Scholar 

  29. Imsick BG, Acharya JR, Nesterov EE (2013) Adv Mater 25(1):120–124

    Article  CAS  Google Scholar 

  30. 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

    Article  CAS  Google Scholar 

  31. Adachi N, Kaneko Y, Sekiguchi K, Sugiyama H, Sugeno M (2015) Luminescence 30(8):1308–1312

    Article  CAS  Google Scholar 

  32. Adachi N, Nakajima M, Okada M, Sugeno M, Norioka T (2016) Polym Adv Technol 27(3):284–289

    Article  CAS  Google Scholar 

  33. 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

    Article  CAS  Google Scholar 

  34. Kim I-B, Bunz UHF (2006) J Am Chem Soc 128(9):2818–2819

    Article  CAS  Google Scholar 

  35. Kim I-B, Dunkhorst A, Bunz UHF (2005) Langmuir 21(17):7985–7989

    Article  CAS  Google Scholar 

  36. Xu H, Wu W, Chen Y, Qiu T, Fan L-J (2014) ACS Appl Mater Interfaces 6(7):5041–5049

    Article  CAS  Google Scholar 

  37. Ma JC, Dougherty DA (1997) Chem Rev 97(5):1303–1324

    Article  CAS  Google Scholar 

  38. Maynor MS, Deason TK, Nelson TL, Lavigne JJ (2009) Supramol Chem 21(3–4):310–315

    Article  CAS  Google Scholar 

  39. 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

    Article  CAS  Google Scholar 

  40. Lv Y, Wu J, Wu P, Chen YZ, Tan Y, Tan C, Jiang Y (2016) RSC Adv 6(48):42443–42446

    Article  CAS  Google Scholar 

  41. Wu D, Schanze KS (2014) ACS Appl Mater Interfaces 6(10):7643–7651

    Article  CAS  Google Scholar 

  42. Dou WT, Zeng YL, Lv Y, Wu J, He XP, Chen GR, Tan C (2016) ACS Appl Mater Inter 8(21):13601–13606

    Article  CAS  Google Scholar 

  43. Niamnont N, Mungkarndee R, Techakriengkrai I, Rashatasakhon P, Sukwattanasinitt M (2010) Bios Bioelectron 26(2):863–867

    Article  CAS  Google Scholar 

  44. Sun P, Lu X, Fan Q, Zhang Z, Song W, Li B, Huang L, Peng J, Huang W (2011) Macromolecules 44:8763–8770

    Article  CAS  Google Scholar 

  45. Yao Z, Feng X, Hong W, Li C, Shi G (2009) Chem Commun 31:4696–4698

    Article  Google Scholar 

  46. Kim IB, Han MH, Phillips RL, Samanta B, Rotello VM, Bunz UHF (2009) Chem Eur J 15:449–456

    Article  CAS  Google Scholar 

  47. Pun CC, Lee K, Kim HJ, Kim J (2006) Macromolecules 39:7461–7463

    Article  CAS  Google Scholar 

  48. Yang Q, Dong Y, Wu W, Zhu C, Chong H, Lu J, Yu D, Liu L, Lv F, Wang S (2012) Nat Commun 3:1206

    Article  Google Scholar 

  49. Phillips RL, Miranda OR, You CC, Rotello VM, Bunz UHF (2008) Angew Chem Int Ed 47:2590–2594

    Article  CAS  Google Scholar 

  50. Golabi M, Turner APF, Jager EWH (2016) Sens Actuators B 222:839–848

    Article  CAS  Google Scholar 

  51. Chen H, Wang B, Zhang J, Nie C, Lv F, Liu L, Wang S (2015) Chem Commun 51:4036–4039

    Article  CAS  Google Scholar 

  52. Satrijo A, Swager TM (2007) J Am Chem Soc 129:16020–16028

    Article  CAS  Google Scholar 

  53. Maynor MS, Nelson TL, O’Sulliva C, Lavigne JJ (2007) Org Lett 9(17):3217–3220

    Article  CAS  Google Scholar 

  54. Cai M, Daniel SL, Lavigne JJ (2013) Chem Commun 49:6504–6506

    Article  CAS  Google Scholar 

  55. Rochat S, Swager TM (2014) Angew Chem Int Ed 53(37):9792–9796

    Article  CAS  Google Scholar 

  56. He C, He Q, Deng C, Shi L, Fu Y, Cao H, Cheng J (2011) Syn Met 161(3–4):293–297

    Article  CAS  Google Scholar 

  57. Kimura M, Sakai R, Sato S, Fukawa T, Ikehara T, Maeda R, Mihara T (2012) Adv Funct Mater 22:469–476

    Article  CAS  Google Scholar 

  58. Chang JB, Liu V, Subramanian V, Sivula K, Luscombe C, Murphy A, Liu J, Fréchet JMJ (2006) J Appl Phys 100:014506

    Article  Google Scholar 

  59. Borzin E, Shemesh A, Hertzog-Ronen C, Gerchikov Y, Tessler N, Eichen Y (2010) J Phys Org Chem 23:1108–1113

    Article  CAS  Google Scholar 

  60. Hertzog-Ronen C, Borzin E, Gerchikov Y, Tessler N, Eichen Y (2009) Chem Eur J 15:10380–10386

    Article  CAS  Google Scholar 

  61. Liao HC, Hsu CP, Wu MC, Lu CF, Su WF (2013) Anal Chem 85(19):9305–9311

    Article  CAS  Google Scholar 

  62. Gonçalves VC, Balogh DT (2009) Sens Actuators B 142:55–60

    Article  Google Scholar 

  63. Si P, Mortensen J, Komolov A, Denborg J, Moller PJ (2007) Anal Chim Acta 597:223–230

    Article  CAS  Google Scholar 

  64. Han J, Wang B, Bender M, Seehafer K, Bunz UHF (2016) ACS Appl Mater Interfaces 8:20415–20421

    Article  CAS  Google Scholar 

  65. Costa AI, Pinto HD, Ferreira LF, Prata JV (2012) Sens Actuators B 161:702–713

    Article  CAS  Google Scholar 

  66. Wu J, Tan C, Chen Z, Chen YZ, Tan Y, Jiang Y (2016) Analyst 141:3242–3245

    Article  CAS  Google Scholar 

  67. Elci SG, Moyano DF, Rana S, Tonga GY, Phillips RL, Bunz UHF, Rotello VM (2013) Chem Sci 4:2076

    Article  CAS  Google Scholar 

  68. Pu K, Zhan R, Liang J, Liu B (2011) Sci China Chem 54:567–574

    Article  CAS  Google Scholar 

Download references

Author information

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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Felix Hinkel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Daniel Jänsch
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Uwe H. F. Bunz
    View author publications

    You can also search for this author in PubMed Google Scholar

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.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

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

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s41061-017-0155-2

Keywords

Search

Navigation