Skip to main content
SpringerLink
Log in

Effect of alkyl chain length on chemical sensing of polydiacetylene and polydiacetylene/ZnO nanocomposites

  • Original Contribution
  • Published:
Colloid and Polymer Science Aims and scope Submit manuscript

Abstract

Polydiacetylenes (PDAs) and PDA/ZnO nanocomposites based on the monomers 10,12-pentacosadiynoic acid (PCDA), 10,12-tricosadiynoic acid (TCDA), and 10,12-docosadiynedioic acid (DCDA) monomers have been investigated for chromatic chemical sensing of a number of organic liquids. Chromatic sensitivity is associated with the interaction of the organic liquid with the PDA side chain to give rise to the strain-induced blue to red colorimetric transition. Attenuated total reflection (ATR) Fourier transform infrared (FTIR) spectroscopy demonstrated that in the PDA/ZnO nanocomposites, the PDA side chains form chelates with ZnO. The chromatic properties of PDAs and PDA/ZnO composites in organic liquids, to certain extent, depend on the side-chain length and the number of carboxylic head groups. Pure PDAs and PDA/ZnO nanocomposites in different organic liquids studied by Raman spectroscopy show that the chromatic selectivity of PDAs for certain organic liquids with respect to the blue to red phase transition is closely related to the side-chain structure of the PDAs. Moreover, the interactions are stronger with those PDAs where the blue to red transition is irreversible. Density functional theory (DFT) simulations show that the chromatic sensitivity of the PDAs toward a particular organic correlates with the C–C bond torsion angle of the PDA backbone.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Descalzo AB, Dolores Marcos M, Monte C, Martinez-Manez R, Rurack K (2007) Mesoporous silica materials with covalently anchored phenoxazinone dyes as fluorescent hybrid materials for vapour sensing. J Mater Chem 17:4716–4723

    Article  CAS  Google Scholar 

  2. Janzen MC, Ponder JB, Bailey DP, Ingison CK, Suslick KS (2006) Colorimetric sensor arrays for volatile organic compounds. Anal Chem 78:3591–3600

    Article  CAS  Google Scholar 

  3. Lu Y, Yang Y, Sellinger A, Lu M, Huang J, Fan H et al (2001) Self-assembly of mesoscopically ordered chromatic polydiacetylene/silica nanocomposites. Nature 410:913–917

    Article  CAS  Google Scholar 

  4. Muro ML, Daws CA, Castellano FN (2008) Microarray pattern recognition based on PtII terpyridyl chloride complexes: vapochromic and vapoluminescent response. Chem Commun (46):6134-6. doi: 10.1039/b812634h

  5. Rakow NA, Suslick KS (2000) A colorimetric sensor array for odour visualization. Nature 406:710–713

    Article  CAS  Google Scholar 

  6. Champaiboon T, Tumcharern G, Potisatityuenyong A, Wacharasindhu S, Sukwattanasinitt M (2009) A polydiacetylene multilayer film for naked eye detection of aromatic compounds. Sensors Actuators B Chem 139:532–537

    Article  CAS  Google Scholar 

  7. Jiang H, Wang Y, Ye Q, Zou G, Su W, Zhang Q (2010) Polydiacetylene-based colorimetric sensor microarray for volatile organic compounds. Sensors Actuators B Chem 143:789–794

    Article  CAS  Google Scholar 

  8. Pumtang S, Siripornnoppakhun W, Sukwattanasinitt M, Ajavakom A (2011) Solvent colorimetric paper-based polydiacetylene sensors from diacetylene lipids. J Colloid Interface Sci 364:366–372

    Article  CAS  Google Scholar 

  9. Hammond PT, Rubner MF (1997) Thermochromism in liquid crystalline polydiacetylenes. Macromolecules 30:5773–5782

    Article  CAS  Google Scholar 

  10. Huang X, Jiang S, Liu M (2004) Metal ion modulated organization and function of the Langmuir-Blodgett films of amphiphilic diacetylene: photopolymerization, thermochromism, and supramolecular chirality. J Phys Chem B 109:114–119

    Article  Google Scholar 

  11. Peng H, Tang J, Pang J, Chen D, Yang L, Ashbaugh HS et al (2005) Polydiacetylene/silica nanocomposites with tunable mesostructure and thermochromatism from diacetylenic assembling molecules. J Am Chem Soc 127:12782–12783

    Article  CAS  Google Scholar 

  12. Kim JM, Lee YB, Chae SK, Ahn DJ (2006) Patterned color and fluorescent images with polydiacetylene supramolecules embedded in poly(vinyl alcohol) films. Adv Funct Mater 16:2103–2109

    Article  CAS  Google Scholar 

  13. Lee S, Kim JM (2007) Alpha-cyclodextrin: a molecule for testing colorimetric reversibility of polydiacetylene supramolecules. Macromolecules 40:9201–9204

    Article  CAS  Google Scholar 

  14. Park H, Lee JS, Choi H, Ahn DJ, Kim JM (2007) Rational design of supramolecular conjugated polymers displaying unusual colorimetric stability upon thermal stress. Adv Funct Mater 17:3447–3455

    Article  CAS  Google Scholar 

  15. Batchelder DN, Evans SD, Freeman TL, Haeussling L, Ringsdorf H, Wolf H (1994) Self-assembled monolayers containing polydiacetylenes. J Am Chem Soc 116:1050–1053

    Article  CAS  Google Scholar 

  16. Baughman RH (1972) Solid-state polymerization of diacetylenes. J Appl Phys 43:4362–4370

    Article  CAS  Google Scholar 

  17. Robert WC, Darryl YS, Matthew SM, Eriksson MA, Alan RB (2004) Polydiacetylene films: a review of recent investigations into chromogenic transitions and nanomechanical properties. J Phys Condens Matter 16:R679–R697

    Article  Google Scholar 

  18. Chanakul A, Traiphol N, Traiphol R (2013) Controlling the reversible thermochromism of polydiacetylene/zinc oxide nanocomposites by varying alkyl chain length. J Colloid Interface Sci 389:106–114

    Article  CAS  Google Scholar 

  19. Charoenthai N, Pattanatornchai T, Wacharasindhu S, Sukwattanasinitt M, Traiphol R (2011) Roles of head group architecture and side chain length on colorimetric response of polydiacetylene vesicles to temperature, ethanol and pH. J Colloid Interface Sci 360:565–573

    Article  CAS  Google Scholar 

  20. Gou M, Guo G, Zhang J, Men K, Song J, Luo F et al (2010) Time–temperature chromatic sensor based on polydiacetylene (PDA) vesicle and amphiphilic copolymer. Sensors Actuators B Chem 150:406–411

    Article  CAS  Google Scholar 

  21. Ryu S, Yoo I, Song S, Yoon B, Kim J-M (2009) A thermoresponsive fluorogenic conjugated polymer for a temperature sensor in microfluidic devices. J Am Chem Soc 131:3800–3801

    Article  CAS  Google Scholar 

  22. Traiphol N, Rungruangviriya N, Potai R, Traiphol R (2011) Stable polydiacetylene/ZnO nanocomposites with two-steps reversible and irreversible thermochromism: the influence of strong surface anchoring. J Colloid Interface Sci 356:481–489

    Article  CAS  Google Scholar 

  23. Peng H, Sun X, Cai F, Chen X, Zhu Y, Liao G et al (2009) Electrochromatic carbon nanotube/polydiacetylene nanocomposite fibres. Nat Nanotechnol 4:738–741

    Article  CAS  Google Scholar 

  24. Yoon B, Ham D-Y, Yarimaga O, An H, Lee CW, Kim J-M (2011) Inkjet printing of conjugated polymer precursors on paper substrates for colorimetric sensing and flexible electrothermochromic display. Adv Mater 23:5492–5497

    Article  CAS  Google Scholar 

  25. Gatebe E, Herron H, Zakeri R, Ramiah Rajasekaran P, Aouadi S, Kohli P (2008) Synthesis and characterization of polydiacetylene films and nanotubes. Langmuir 24:11947–11954

    Article  CAS  Google Scholar 

  26. Patlolla A, Zunino J, Frenkel AI, Iqbal Z (2012) Thermochromism in polydiacetylene-metal oxide nanocomposites. J Mater Chem 22:7028–7035

    Article  CAS  Google Scholar 

  27. Wu A, Beck C, Ying Y, Federici J, Iqbal Z (2013) Thermochromism in polydiacetylene–ZnO nanocomposites. J Phys Chem C 117:19593–19600

    CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge support by ARDEC, Picatinny Arsenal, and CarboMet LLC.

Author information

Authors and Affiliations

  1. Department of Physics, New Jersey Institute of Technology, Newark, NJ, 07102, USA

    Aide Wu, Yuan Gu & John F. Federici

  2. Department of Chemistry and Environmental Science, New Jersey Institute of Technology, Newark, NJ, 07102, USA

    Zafar Iqbal

  3. Key Laboratory of Computational Geodynamics, University of Chinese Academy of Science, Beijing, 100049, China

    Huiquan Tian

Authors
  1. Aide Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yuan Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Huiquan Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. John F. Federici
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Zafar Iqbal
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Aide Wu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Figure S1

(DOCX 156 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, A., Gu, Y., Tian, H. et al. Effect of alkyl chain length on chemical sensing of polydiacetylene and polydiacetylene/ZnO nanocomposites. Colloid Polym Sci 292, 3137–3146 (2014). https://doi.org/10.1007/s00396-014-3365-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00396-014-3365-y

Keywords

Search

Navigation