Abstract
This first chapter gives a general overview of the surface modification by diazonium salts: the different methods that permit to attach aryl groups to surfaces, the characterization of the bond between the surface and the organic film, the mechanism of the grafting reaction, the structure of the organic film, the different groups that can functionalize the substrates, the different emerging substrates. In each case, we emphasize the most recent results and we refer the reader to the different chapters for additional information. In a final section, we describe an original method that permits, starting from a specially designed diazonium salt, grafting of a wide variety of different molecules such as, for example, organic halides, acetonitrile, methylamine. This method is based on atom abstraction and could apply to large range of molecules.
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References
Pujari SP, Scheres L, Marcelis ATM, Zuilhof H (2014) Angew Chem Int Ed 53:6322–6356. https://doi.org/10.1002/anie.201306709
Vericat C, Vela ME, Benitez G, Carro P, Salvarezza RC (2010) Chem Soc Rev 39:1805–1834. https://doi.org/10.1039/b907301a
Hetemi D, Pinson J (2017) Chem Soc Rev 46:5701–5713. https://doi.org/10.1039/c7cs00150a
Pinson J, Thiry D (eds) (2020) Surface modification of polymers: methods and applications. Wiley, Weinheim, Germany. ISBN: 978-3-527-81923-2
Mo F, Qiu D, Zhang L, Wang J (2021) Chem Rev 121:5741–5829. https://doi.org/10.1021/acs.chemrev.0c01030
Pinson J, Podvorica FI (2020) Curr Opin Electrochem 24:44–48
Berisha A, Chehimi MM, Pinson J, Podvorica FI (2016) Electrode surface modification using diazonium salts. In: Bard AJ, Zoski CG (eds) Electroanalytical chemistry, vol 26. CRC Press, Boca Raton, FL. ISBN:978-1-498763377-9
Chehimi MM (ed) (2012) Aryl Diazonium salts. New coupling agents in polymer and surface science. Wiley-VCH, Weinheim, Germany, ISBN: 978-3-527-32998-4
Mahouche-Chergui S, Gam-Derouich S, Mangeney C, Chehimi MM (2011) Chem Soc Rev 40:4143–4166. https://doi.org/10.1039/c0cs00179a
Gooding JJ, Ciampi S (2011) Chem Soc Rev 40:2704–2718. https://doi.org/10.1039/C0CS00139B
Bélanger D, Pinson J (2011) Chem Soc Rev 40:3995–4048. https://doi.org/10.1039/c0cs00149j
Pinson J, Podvorica F (2005) Chem Soc Rev 34:429–439. https://doi.org/10.1039/b406228k
Vase KH, Holm AH, Pedersen SU, Daasbjerg K (2005) Langmuir 21:8085–8089. https://doi.org/10.1021/la050933e
Koefoed L, Pedersen SU, Daasbjerg K (2016) ChemElectroChem 3:495–501. https://doi.org/10.1002/celc.201500512
Wang D, Buriak JM (2005) Surf Sci 590:154–161. https://doi.org/10.1016/j.susc.2005.06.018
Chehimi MM, Hallais G, Matrab T, Pinson J, Podvorica FI (2008) J Phys Chem C 112:18559–18565. https://doi.org/10.1021/jp807044j
Médard J, Decorse P, Mangeney C, Pinson J, Fagnoni M, Protti S (2020) Langmuir 36:2786–2793. https://doi.org/10.1021/acs.langmuir.9b03878
Adenier A, Chehimi MM, Gallardo I, Pinson J, Vilà N (2004) Langmuir 20:8243–8253. https://doi.org/10.1021/la049194c
Hernández-Muñoz LS, González-Fuentes MA, Díaz-Sánchez BR, Fragoso-Soriano R, Vázquez-López C, González FJ (2012) Electrochim Acta 63:287–294. https://doi.org/10.1016/j.electacta.2014.04.189
Li D, Luo Y, Onidas D, He L, Jin M, Gazeau F, Pinson J, Mangeney C (2021) Adv Colloid Interface Sci 294:102479
Delamar M, Hitmi R, Pinson J, Savéant J-M (1992) J Am Chem Soc 114:5883–5884. https://doi.org/10.1021/ja00040a074
Allongue P, Delamar M, Desbat B, Fagebaume O, Hitmi R, Pinson J, Savéant J-M (1997) J Am Chem Soc 119:201–207. https://doi.org/10.1021/ja963354s
Hetemi D, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2016) Elec Comm 68:5–9. https://doi.org/10.1016/j.elecom.2016.04.001
Richard W, Evrard D, Busson B, Humbert C, Dalstein L, Tadjeddine A, Gros P (2018) Electrochim Acta 283:1640–1648. https://doi.org/10.1016/j.electacta.2018.07.073
Lenne Q, Andrieux V, Levanen G, Bergamini J-F, Nicolas P, Paquin L, Lagrost C, Yann R, Leroux YR (2021) Electrochimica Acta 369: 137672. https://doi.org/10.1016/j.electacta.2020.137672
Benedetto A, Balog M, Viel P, Le Derf F, Sallé M, Palacin S (2008) Electrochim Acta 53:7117–7122. https://doi.org/10.1016/j.electacta.2008.05.001
Lee L, Brooksby PA, Hapiot P, Downard AJ (2016) Langmuir 32:468–476. https://doi.org/10.1021/acs.langmuir.5b03233
Koefoed L, Vase KH, Stenlid JH, Brinck T, Yoshimura Y, Lund H, Pedersen SU, Daasbjerg K (2017) ChemElectroChem 4:3212–3221. https://doi.org/10.1002/celc.201700772
Romanczyk PP, Kurek SS (2020) Electrochim Acta 351:136404. https://doi.org/10.1016/j.electacta.2020.136404
Koefoed L, Pedersen SU, Daasbjerg K (2017) Langmuir 33:3217–3222. https://doi.org/10.1021/acs.langmuir.7b00300
Raviola C, Protti S (2020) Eur J Org Chem 33:5292–5304. https://doi.org/10.1002/ejoc.202000143
Hari DP, Hering T, Koenig B (2018) Arene functionalization by visible light photoredox catalysis in visible light photocatalysis in organic chemistry. In: Stephenson C, Tehshik Y, MacMillan DWC (eds). Wiley VCH, pp 253–281. https://doi.org/10.1002/9783527674145
Bouriga M, Chehimi MM, Combellas C, Decorse P, Kanoufi F, Deronzier A, Pinson J (2013) Chem Mater 25:90–97. https://doi.org/10.1021/cm3032994
Busson M, Berisha A, Combellas C, Kanoufi F, Pinson J (2011) Chem Commun 47:12631–12633. https://doi.org/10.1039/c1cc16241a
Verberne-Sutton SD, Quarels RD, Zhai X, Garno JC, Ragains JR (2014) J Am Chem Soc 136:14438–14444. https://doi.org/10.1021/ja505521k
Médard J, Combellas C, Kanoufi F, Pinson J, Chauvin J, Deronzier A (2018) J Phys Chem C 122:19722–19730. https://doi.org/10.1021/acs.jpcc.8b06541
Schroll P, Fehl C, Dankesreiter S, König B (2013) Org Biomol Chem 11:6510–6514. https://doi.org/10.1039/c3ob40990b
Garcia A, Hanifi N, Jousselme B, Jégou J, Palacin S, Viel P, Berthelot T (2013) Adv Funct Mater 23:3668–3674. https://doi.org/10.1002/adfm.201203544
Sergeeva NN, Chaika AN, Walls B, Murphy BE, Walshe K, Martin DP, Richards BDO, Jose G, Fleischer K, Aristov VU, Molodtsova OV, Shvets IV, Krasnikov SA (2018) Nanotechnology 29:275705. https://doi.org/10.1088/1361-6528/aabf11
González MCR, Brown A, Eyley S, Thielemans W, Mali KS De Feyter S (2020) Nanoscale12:18782. https://doi.org/10.1039/d0nr05244b
Zeb G, Viel P, Palacin S, Le XT (2015) RSC Adv 5:50298–50305. https://doi.org/10.1039/c5ra07875j
Mevellec V, Roussel S, Tessier L, Chancolon J, Mayne-L’Hermite M, Deniau G, Viel P, Palacin S (2007) Chem Mater 19:6323–6330. https://doi.org/10.1021/cm071371i
Enciso AE, Doni G, Nifosì R, Palazzesi F, Gonzalez R, Ellsworth AA, Coffer JL, Walker AV, Giovanni M. Pavan GM, Mohamed AM, Simanek EE (2017) Nanoscale 9:3128–3132. https://doi.org/10.1039/c6nr09679d
Xia Y, Martin C, Seibel J, Eyley S, Thielemans W, van der Auweraer M, Mali KS, De Feyter S (2020) Nanoscale 12:11916–11926. https://doi.org/10.1039/d0nr03309j
Adenier A, Cabet-Deliry E, Chaussé A, Griveau S, Mercier F, Pinson J, Vautrin-Ul (2005) Chem Mater 17:491–501. https://doi.org/10.1021/cm0490625
Hurley BL, McCreery RL (2004) J Electrochem Soc 151:B252-259. https://doi.org/10.1149/1.1687428
Combellas C, Delamar M, Kanoufi F, Pinson J, Podvorica F (2005) Chem Mater 17:3968–3975. https://doi.org/10.1021/cm050339q
Lehr J, Williamson BE, Downard AJ (2011) J Phys Chem C 115:6629–6634. https://doi.org/10.1021/jp111838r
Berisha A, Hazimeh H, Galtayries A, Decorse P, Kanoufi F, Combellas C, Pinson J, Podvorica FI (2016) RSC Adv 6:78369–78376. https://doi.org/10.1039/c6ra15313e
Squillace O, Perrault T, Gorczynska M, Caruana A, Bajorek A, Brotons G (2021) Colloids Surf B 197:111427. https://doi.org/10.1016/j.colsurfb.2020.111427
Delaporte N, Trudeau ML, Bélanger D, Zaghib K (2020) Materials 13:942. https://doi.org/10.3390/ma13040942
Luo Y, Xiao Y, Onidas D, Iannazzo L, Ethève-Quelquejeu M, Lamouri A, Félidj N, Mahouche-Chergui S, Brulé T, Gagey-Eilstein N, Gazeau F, Mangeney C (2020) Chem Commun 56:6822–6825. https://doi.org/10.1039/d0cc02842h
Lei Y, Huang Q, Gan D, Huang H, Chen J, Deng F, Liu M, Li X, Zhanga X, Wei Y (2020) J Environ Chem Engin 8:103780. https://doi.org/10.1016/j.jece.2020.103780
Griffete N, Herbst F, Pinson J, Ammar S, Mangeney C (2011) J Am Chem Soc 133:1646–1649. https://doi.org/10.1021/ja108928
Chenga C, Jia P, Xiao L, Geng J (2019) Carbon 145:668–676. https://doi.org/10.1016/j.carbon.2019.01.079
Mamane V, Mercier G, Shukor JA, Gleize J, Azizan A, Fort Y, Vigolo B (2014) Beilstein J Nanotechnol 5:537–545. https://doi.org/10.3762/bjnano.5.63
Van Druenen M, Davitt F, Collins T, Glynn C, O’Dwyer C, Holmes JD, Collin G (2018) Chem Mater 30:4667–4674. https://doi.org/10.1021/acs.chemmater.8b01306
Güell AG, Roodenko K, Yang F, Hinrichs K, Gensch M, Sanz F, Rappich J (2006) Mater Sci Eng B 134:273–276. https://doi.org/10.1016/j.mseb.2006.07.005
Hinge M, Gonçalves ES, Pedersen SU, Daasbjerg K (2010) Surf Coat Technol 205:820–827. https://doi.org/10.1016/j.surfcoat.2010.07.125
Gorp HV, Walke P, Teyssandier J, Hirsch BE, Uji-i H, Tahara K, Tobe Y, Van der Auweraer M, De Feyter S (2020) J Phys Chem C 124:1980–1990. https://doi.org/10.1021/acs.jpcc.9b09808
Schirowski M, Hauke F, Hirsch A (2019) Chem Eur J 25:12761–12768. https://doi.org/10.1002/chem.201902330
Laurentius L, Stoyanov SR, Gusarov S, Kovalenko A, Du R, Lopinski GP, McDermott MT (2011) ACS Nano 5:4219–4227. https://doi.org/10.1021/nn201110r
Barosi A, Berisha A, Mangeney C, Pinson J, Dhimane, Dalko PI (2021) Mater Adv 2:2358–2365. https://doi.org/10.1039/d1ma00022e
Berisha A, Combellas C, Kanoufi F, Médard J, Decorse P, Mangeney C, Kherbouche I, Seydou, M, Maurel F, Pinson J (2018) Langmuir 34:11264−11271. https://doi.org/10.1021/acs.langmuir.8b01584
Li H, Kopiec G, Müller F, Nyßen F, Shimizu K, Ceccato M, Daasbjerg K, Plumeré N (2020) J Am Chem Soc Au 142:8662–8671. https://doi.org/10.1021/jacsau.0c00108
Greenwood J, Phan TH, Fujita Y, Li Z, Ivasenko O, Vanderlinden W, Van Gorp H, Frederickx W, Lu G, Tahara K, Tobe Y, Uji-i H, Mertens SFL, De Feyter S (2015) ACS Nano 5:5520–5525. https://doi.org/10.1021/acsnano.5b01580
Sampathkumar K, Diez-Cabanes V, Kovaricek P, del Corro E, Bouša M, Hošek J, Kalbac M, Frank O (2019) J Phys Chem C 123:22397–22402. https://doi.org/10.1021/acs.jpcc.9b06516
Ossonon BD, Bélanger D (2017) Carbon 111:83–93. https://doi.org/10.1016/j.carbon.2016.09.063
Brymora K, Fouineau J, Eddarir A, Chau F, Yaacoub N, Grenèche J-M, Pinson J, Ammar S, Calvayrac F (2015) J Nanopart Res 17:438. https://doi.org/10.1007/s11051-015-3232-x
Betelu S, Tijunelyte I, Boubekeur-Lecaque L, Ignatiadis I, Ibrahim J, Gaboreau S, Berho C, Toury T. Guenin E, Lidgi-Guigui N, Félidj N, Rinnert E, Lamy de la Chapelle M (2016) J Phys Chem C 120:18158–18166. https://doi.org/10.1021/acs.jpcc.6b06486
Mesnage A, Lefèvre X, Jégou P, Deniau G, Palacin S (2012) Langmuir 28:11767–11778. https://doi.org/10.1021/la3011103
Berisha A (2019) J Chem 5126071. https://doi.org/10.1155/2019/5126071
Kong L, Enders A, Rahman TS, Dowben PA (2014) J Phys: Condens Matter 26:443001. https://doi.org/10.1088/0953-8984/26/44/443001
Gross AJ, Tanaka S, Colomies C, Giroud F, Nishina Y, Cosnier S, Tsujimura S, Holzinger M (2020) ChemElectroChem 7:4543–4549. https://doi.org/10.1002/celc.202000953
Le Comte A, Chhin D, Gagnon A, Retoux R, Brousse T, Bélanger D (2015) J Mater Chem A 3:6146–6156. https://doi.org/10.1039/c4ta05536e
Berisha A, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2011) Electrochim Acta 56:10762–10766. https://doi.org/10.1016/j.electacta.2011.01.049
Morales-Martínez D, Lartundo-Rojas L, González FJ (2020) ChemElectroChem 7:4431–4439. https://doi.org/10.1002/celc.202001096
Mesnage A, Esnouf S, Jégou P, Deniau G, Palacin S (2010) Chem Mater 22:6229–6239. https://doi.org/10.1021/cm1014702
Schmidt G, Gallon S, Esnouf S, Bourgoin J-P, Chenevier P (2009) Chem Eur J 15:2101–2110. https://doi.org/10.1002/chem.200801801
Lohmann S-H, Trerayapiwat KJ, Niklas J, Poluektov OG, Sharifzadeh S, Ma X (2020) ACS Nano 14:17675–17682. https://doi.org/10.1021/acsnano.0c08782
Suehiro T, Masuda S, Tashiro T, Nakausa R, Taguchi M, Koike A, Rieker A (1986) Bull Chem Soc Jpn 59:1877–1886. https://doi.org/10.1246/bcsj.59.1877
Doppelt P, Hallais G, Pinson J, Podvorica F, Verneyre S (2007) Chem Mater 19:4570–4575. https://doi.org/10.1021/cm0700551
Berisha A, Combellas C, Kanoufi F, Decorse F, Oturan N, Médard J, Seydou M, Maurel F, Pinson J (2017) Langmuir 33:8730−8738. https://doi.org/10.1021/acs.langmuir.7b01371
Buriak JM, Sikder MdDH (2015) J Am Chem Soc 137:9730–9738. https://doi.org/10.1021/jacs.5b05738
Ait El Hadj F, Amiar A, Cherkaoui M, Chazalviel J-N, Ozanam F (2012) Electrochim Acta 70: 318–324. https://doi.org/10.1016/j.electacta.2012.03.072
Henry de Villeneuve C, Pinson J, Bernard MC, Allongue P (1997) J Phys Chem B 101:2415–2420. https://doi.org/10.1021/jp962581d
Chehimi MM, Lamouri A, Picot M, Pinson J (2014) J Mater Chem C 2:356–363. https://doi.org/10.1039/c3tc31492h
Jayasundara DR, Cullen RJ, Soldi L, Colavita PE (2011) Langmuir 27:13029–13036. https://doi.org/10.1021/la202862p
Han X, Lee HK, Lee YH, Hao W, Liu Y, Phang IY, Li S, Ling XY (2016) J Phys Chem Lett 7:1501–1506. https://doi.org/10.1021/acs.jpclett.6b00501
Bouden S, Pinson J, Vautrin-Ul C (2017) Electrochem Com 81:120–123. https://doi.org/10.1016/j.elecom.2017.06.007
Shkirskiy V, Levillain E, Gautier C (2021) ChemPhysChem 22:1074–1078. https://doi.org/10.1002/cphc.202100154
Allongue P, Henry de Villeneuve C, Cherouvrier G, Cortes R, Bernard, MC (2003) J Electroanal Chem 550–551:161–174. https://doi.org/10.1016/S0022-0728(03)00076-7
Anariba F, Viswanathan U, Bocian DF, McCreery RL (2006) Anal Chem 78:3104–3112. https://doi.org/10.1021/ac052042h
Podvorica FI, Kanoufi F, Pinson J, Combellas C (2009) Electrochim Acta 54:2164–2170. https://doi.org/10.1016/j.electacta.2008.10.017
Fontaine O, Ghilane J, Martin P, Lacroix J-C, Randriamahazaka H (2010) Langmuir 26:18542–18549. https://doi.org/10.1021/la103000u
Nielsen LT, Vase KH, Dong M, Besenbacher F, Pedersen SU, Daasbjerg K (2007) J Am Chem Soc 129:1888–1889. https://doi.org/10.1021/ja0682430
Yates ND, Dowsett MR, Bentley P, Dickenson-Fogg JA, Pratt A, Blanford CF, Fascione MA, Parkin A (2020) Langmuir 36:5654–5664. https://doi.org/10.1021/acs.langmuir.9b01254
Combellas C, Kanoufi F, Pinson J, Podvorica FI (2008) J Am Chem Soc 130:8576–8577. https://doi.org/10.1021/ja8018912
Gillan L, Teerinen T, Johansson L-S, Smolander M (2020) Sensor Int 2:100060. https://doi.org/10.1016/j.sintl.2020.100060
Nguyen VQ, Sun X, Lafolet F, Audibert JF, Miomandre F, Lemercier G, Loiseau F, Lacroix JC (2016) J Am Chem Soc 138:9381–9384. https://doi.org/10.1021/jacs.6b04827
Leroux YR, Hui F, Noël JM, Roux C, Hapiot P (2010) J Am Chem Soc 132:14039–14041. https://doi.org/10.1021/ja106971x
Troian-Gautier L, Martinez-Tong DE, Hubert J, Reniers F, Sferrazza M, Mattiuzzi A, Lagrost C, Jabin I (2016) J Phys Chem C 120:22936–22945. https://doi.org/10.1021/acs.jpcc.6b06143
Menanteau T, Levillain E, Breton T (2013) Chem Mater 25:2905–2909. https://doi.org/10.1021/cm401512c
López I, Dabos-Seignon S, Breton T (2019) Langmuir 35:11048–11055. https://doi.org/10.1021/acs.langmuir.9b01397
Rodríguez González MC, Brown A, Eyley S, Thielemans W, Mali KS, De Feyter S (2020) Nanoscale 12:18782–18789. https://doi.org/10.1039/D0NR05244B
Gabaji M, Médard J, Hemmerle A, Pinson J, Michel JP (2020) Langmuir 36:2534−2542. https://doi.org/10.1021/acs.langmuir.9b03601
Lee L, Leroux YR, Hapiot P, Downard AJ (2015) Langmuir 31:5071–5077. https://doi.org/10.1021/acs.langmuir.5b00730
Hetemi D, Noël V, Pinson J (2020) Biosensors 10:4. https://doi.org/10.3390/bios10010004
Sayed SY, Bayat A, Kondratenko M, Leroux Y, Hapiot P, McCreery RL (2013) J Am Chem Soc 135:12972–12975. https://doi.org/10.1021/ja4065443
Wang A, Ye J, Humphrey MG, Zhang C (2018) Adv Mater 30:1705704. https://doi.org/10.1002/adma.201705704
Adenier A, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2006) Chem Mater 18:2021–2029. https://doi.org/10.1021/cm052065c
Ceccato M, Bousquet A, Hinge M, Pedersen SU, Daasbjerg K (2011) Chem Mater 23:1551–1557. https://doi.org/10.1021/cm1033244
Evrard D, Lambert F, Policar C, Balland V, Limoges B (2008) Chem Eur J 14:9286–9291. https://doi.org/10.1002/chem.200801168
Downard AJ (2009) Int J Nanotechnol 6:233–244. https://doi.org/10.1504/IJNT.2009.022916
Brooksby PA, Downard AJ (2005) J Phys Chem B 109:8791–8798. https://doi.org/10.1021/jp046095z
Sandomierski M, Voelkel A (2021) J Inorg Organomet Polym Mater 31:1–21. https://doi.org/10.1007/s10904-020-01725-0
Demir B, Henderson LC, Walsh TR (2017) ACS Appl Mater Interfaces 9:11846–11857. https://doi.org/10.1021/acsami.6b16041
Sandomierski M, Buchwald T, Strzemiecka B, Voelke A (2020) J Appl Polym Sci 137:48160. https://doi.org/10.1002/app.48160
Chaussé A, Chehimi MM, Karsi N, Pinson J, Podvorica F, Vautrin-Ul C (2002) Chem Mater 14:392–400. https://doi.org/10.1021/cm011212d
Bernard MC, Chaussé A, Cabet-Deliry E, Chehimi MM, Pinson J, Podvorica F, Vautrin-Ul C (2003) Chem Mater 15:3450–3462. https://doi.org/10.1021/cm034167d
Cui Y, Hu Z-J, Yang J-X, Gao H-W (2012) Microchim Acta 176:359–366. https://doi.org/10.1007/s00604-011-0725-x
Gooding JJ, Ciampi S (2011) Chem Soc Rev 40:2704–2718. https://doi.org/10.1039/C0CS00139B
Gautier C, López I, Breton T (2021) Mater Adv 2:2773–2810. https://doi.org/10.1039/d1ma00077b
Cougnon C, Gohier F, Bélanger D, Mauzeroll J (2009) Angew Chem Int Ed 48:4006–4008. https://doi.org/10.1002/anie.200900498
Corgier BP, Bellon S, Anger-Leroy M, Blum LJ, Marquette CA (2009) Langmuir 25:9619–9623. https://doi.org/10.1021/la900762s
Bouden S, Chaussé A, Dorbes S, El Tall O, Bellakhal N, Dachraoui M, Vautrin-Ul C (2013) Talanta 106:414–421. https://doi.org/10.1016/j.talanta.2013.01.021
Bouden S, Bellakhal N, Chaussé A, Dachraoui M, Vautrin-Ul C (2014) Electrochim Acta 125:149–155. https://doi.org/10.1016/j.electacta.2014.01.083
Eissa S, Zourob M (2021) Anal Chem 93:1826–1833. https://doi.org/10.1021/acs.analchem.0c04719
Qi M, Zhang Y, Cao C, Zhang M, Liu S, Liu G (2016) Anal Chem 88:9614–9621. https://doi.org/10.1021/acs.analchem.6b02353
Rather JA, Khudaish EA, Kannan P (2018) Analyst 143:1835–1845. https://doi.org/10.1039/C7AN02092A
Zhang L, Gao L-F, Li L, Hu C-X, Yang Q-Q, Zhu Z-Y, Peng R, Qiang Wang Q, Peng Y, Jin J, Zhang H-L (2018) Mater Chem Front 2:1700–1706. https://doi.org/10.1039/C8QM00237A
Ok-Kyung P, Jun-Yeon H, Munju G, Joong HL, Bon-Cheol K, Nam-Ho Y (2013) Macromolecules 46:3505–3511. https://doi.org/10.1021/ma400185j
Marshall N, Locklin JJ (2011) Langmuir 27:13367–13373. https://doi.org/10.1021/la2024617
Orchanian NM, Hong LE, Skrainka JA, Esterhuizen JA, Popov DA, Marinescu SC (2019) ACS Appl Energy Mater 2:110–123. https://doi.org/10.1021/acsaem.8b01745
Schirowski M, Abellán G, Nuin E, Pampel J, Dolle C, Wedler V, Fellinger TP, Spiecker E, Hauke F, Hirsch A (2018) J Am Chem Soc 140:3352–3360. https://doi.org/10.1021/jacs.7b12910
Mpeta LS, Sen P, Nyokong T (2020) J Electroanal Chem 860:113896. https://doi.org/10.1016/j.jelechem.2020.113896
Zhang L, Vilà N, Kohring G-W, Walcarius A, Etienne M (2017) ACS Catal 7:4386–4394. https://doi.org/10.1021/acscatal.7b00128
Leroux YR, Fei H, Noël J-M, Roux C, Hapiot P (2010) J Am Chem Soc 132:14039–14041. https://doi.org/10.1021/ja106971x
Yamamoto T, Akahori M, Natsui K, Saitoh T, Einaga Y (2018) Carbon 130:350–354. https://doi.org/10.1016/j.carbon.2017.12.098
Combellas C, Kanoufi F, Pinson J, Podvorica FI (2005) Langmuir 21:280–286. https://doi.org/10.1021/la048106l
Adenier A, Bernard MC, Chehimi MM, Cabet-Deliry E, Desbat B, Fagebaume O, Pinson J, Podvorica F (2001) J Am Chem Soc 123:4541–4549. https://doi.org/10.1021/ja003276f
Gam-Derouich S, Pinson J, Decorse P, Luo Y, Herbaut R, Royon L, Mangeney C (2018) Chem Comm 54:8983–8986. https://doi.org/10.1039/C8CC02601G
Dimé AKD, Bousfiha A, Devillers CH (2020) Curr Opin Electrochem 24:69–78. https://doi.org/10.1016/j.coelec.2020.07.004
Kudas Z, Atmaca U, Saruhan T, Celik M, Ekinci D (2020) Electroanalysis 32:1379–1390. https://doi.org/10.1002/elan.201900707
Marianov AN, Jiang Y (2019) ACS Sustain Chem Eng 7:3838–3848. https://doi.org/10.1021/acssuschemeng.8b04735
Dasler D, Schäfer RA, Minameyer MB, Hitzenberger JF, Hauke F, Drewello T, Hirsch A (2017) J Am Chem Soc 139:11760–11765. https://doi.org/10.1021/jacs.7b04122
Harris TGAA, Gotz R, Wrzolek P, Davis V, Knapp CE, Ly K, Hildebrandt P, Schwalbe M, Weidinger I, Zebger I, Fischer A (2018) J Mater Chem A 6:15200. https://doi.org/10.1039/c8ta02983k
Yao X, Sun X, Lafolet F, Lacroix J-C (2020) Nano Lett 20:6899–6907. https://doi.org/10.1021/acs.nanolett.0c03000
Wang A, Yu W, Huang Z, Zhou F, Song J, Song Y, Long L, Cifuentes MP, Humphrey MG, Zhang L, Shao J, Zhan C (2016) Sci Rep 6:23325. https://doi.org/10.1038/srep23325
Jousselme B, Bidan G, Billon M, Goyer C, Kervella Y, Guillerez S, Hamad EA, Goze-Bac C, Mevellec J-Y, Lefrant S (2008) J Electroanal Chem 621:277–285. https://doi.org/10.1016/j.jelechem.2008.01.026
Blankespoor R, Limoges B, Schoellhorn B, Syssa-Magale JL, Yazidi D (2005) Langmuir 21:3362–3375. https://doi.org/10.1021/la047139y
Tregubov AA, Vuong KQ, Luais E, Gooding JJ, Messerle BA (2013) J Am Chem Soc 135:16429–16437. https://doi.org/10.1021/ja405783g|
Sun C, Rotundo L, Garino C, Nencini L, Yoon SS, Gobetto R, Nervi C (2017) ChemPhysChem 18:3219–3229. https://doi.org/10.1002/cphc.201700739
Jiang C, Silva SM, Fan S, Wu Y, Alam MT, Liu G, Gooding JJ (2017) J Electroanal Chem 785:265–278. https://doi.org/10.1016/j.jelechem.2016.11.043
Liu G, Chockalingham M, Khor SM, Gui AL, Gooding JJ (2010) Electroanalysis 22:918–926. https://doi.org/10.1002/elan.200900539
Zhang L, Vilà N, Walcarius A, Etienne M (2018) ChemElectroChem 5:2208–2217. https://doi.org/10.1002/celc.201800258
Brooksby PA, Downard A (2005) Langmuir 21:1672–1675. https://doi.org/10.1021/la0468848
Downard A, Garret DJ, Tan ESQ (2006) Langmuir 22:10739–10746. https://doi.org/10.1021/la061148k
Corgier BP, Bélanger D (2010) Langmuir 26:5991–5997. https://doi.org/10.1021/la904521w
Nguyen V-Q, Schaming D, Martin P, Lacroix J-C (2019) Langmuir 35:15071–15077. https://doi.org/10.1021/acs.langmuir.9b02811
Leroux YR, Hui F, Noël J-M, Roux C, Downard AJ, Hapiot P (2011) Langmuir 27:11222–11228. https://doi.org/10.1021/la202250y
Mattiuzzi A, Jabin I, Mangeney C, Roux C, Reinaud O, Santos L, Bergamini J-F, Hapiot P, Lagrost C (2012) Nat Commun 3:1130. https://doi.org/10.1038/ncomms2121
Troian-Gautier L, Mattiuzzi A, Reinaud O, Lagrost C, Jabin I (2020) Org Biomol Chem 18:3624–3637. https://doi.org/10.1039/D0OB00070A
Jiang C, Alam MT, Silva SM, Taufik S, Fan S, Gooding JJ (2016) ACS Sensors 1:1432–1438. https://doi.org/10.1021/acssensors.6b00532
Delaporte N, Lajoie G, Collin-Martin S, Zaghib K (2020) Sci Rep 10:3812. https://doi.org/10.1038/s41598-020-60633-y18
Toupin M, Belanger D (2008) Langmuir 24:1910–1917. https://doi.org/10.1021/la702556n
Belmont JA, Amici RM, Galloway CP (1998) Reaction of carbon black with diazonium salts, resultant carbon black products, and their uses. United States, US5851280 A 1998-12-22
Li Z, Yan W, Dai S (2005) Langmuir 21:11999–12006. https://doi.org/10.1021/la051608u
Orchanian NM, Hong LE, Marinescu SC (2019) ACS Catal 9:9393–9397. https://doi.org/10.1021/acscatal.9b03134
Cao N, Guo J, Cai K, Xue Q, Zhu L, Shao Q, Gu X, Zang X (2020) Sep Purif Technol 251:117308. https://doi.org/10.1016/j.seppur.2020.117308
Bensghaier A, Mousli F, Lamouri A, Postnikov PS, Chehimi MM (2020) Chem Afr 3:535–569. https://doi.org/10.1007/s42250-020-00144-5
Unwin PR, Guell AG, Zhang G (2016) Acc Chem Res 49:2041–2048. https://doi.org/10.1021/acs.accounts.6b00301
Hirsch A, Englert JM, Hauke F (2013) Acc Chem Res 46:87–96. https://doi.org/10.1021/ar300116q
Raymakers J, Haenen K, Maes W (2020) J Mater Chem C 7:10134–10165. https://doi.org/10.1039/c9tc03381e
Jacques A, Devillers S, Delhalle J, Mekhalif Z (2013) Electrochim Acta 109:781–789. https://doi.org/10.1016/j.electacta.2013.07.178
Mesnage A, Lefevre X, Jegou P, Deniau G, Palacin S (2012) Langmuir 28:11767–11778. https://doi.org/10.1021/la3011103
Torrens M, Ortiz M, Turner APF, Beni V, O’Sullivan CK (2015) Chem Eur J 21:671–681. https://doi.org/10.1002/chem.201405121
Ghilane J, Delamar M, Guilloux-Viry M, Lagrost C, Mangeney C, Hapiot P (2005) Langmuir 21:6422–6429. https://doi.org/10.1021/la050401y
Atmane YA, Sicard L, Lamouri A, Pinson J, Sicard M, Masson C, Nowak S, Decorse P, Piquemal JY, Galtayries A, Mangeney C (2013) J Phys Chem C 117:26000–26006. https://doi.org/10.1021/jp406356s
Alageel O, Abdallah MN, Luo ZY, Del-Rio-Highsmith J, Cerruti M, Tamimi F (2015) Dent Mater 31:105–114. https://doi.org/10.1016/j.dental.2014.11.002
Le XT, Zeb G, Jegou P, Berthelot T (2012) Electrochim Acta 71:66–72. https://doi.org/10.1016/j.electacta.2012.03.076
Samanta S, Bakas I, Singh A, Aswal DK, Chehimi MM (2014) Langmuir 30:9397–9406. https://doi.org/10.1021/la501909r
Kim YS, Fournier S, Lau-Truong S, Decorse P, Devillers CH, Lucas D, Harris KD, Limoges B, Balland V (2018) ChemElectroChem 5:1625–1630. https://doi.org/10.1002/celc.201800418
Bangle R, Sampaio RN, Troian-Gautier L, Meyer GJ (2018) ACS Appl Mater Interfaces 10:3121–3132. https://doi.org/10.1021/acsami.7b16641
Lamberti F, Agnoli S, Brigo L, Granozzi G, Giomo M, Elvassore N (2013) ACS Appl Mater Interfaces 5:12887–12894. https://doi.org/10.1021/am403292x
Bui-Thi-Tuyet V, Cannizzo C, Legros C, Andrieux M, Chaussé A (2019) Surfaces Interfaces 15:110–116. https://doi.org/10.1016/j.surfin.2019.01.012
McNeill AR, Martinez-Gazoni R, Reeves RJ, Allen MW, Downard AJ (2021) ChemPhysChem 22:1344–1351. https://doi.org/10.1002/cphc.202100240
Buck E, Lee S, Stone LS, Cerruti M (2021) ACS Appl Mater Interfaces 13:7021–7036. https://doi.org/10.1021/acsami.0c16509
Mohamed AA, Neal SN, Atallah B, AlBab ND, Alawadhi HA, Pajouhafsar Y, Abdou HE, Workie B, Sahle-Demessie E, Han C, Monge M, Lopez-de-Luzuriaga JM, Reibenspies JH, Chehimi MM (2018) J Organomet Chem 877:1–11. https://doi.org/10.1016/j.jorganchem.2018.07.032
Ryder CR, Wood JD, Wells SA, Yang Y, Jariwala D, Marks TJ, Schatz GC, Hersam MC (2016) Nat Chem 8:597–602. https://doi.org/10.1038/nchem.2505
Liu G, Gao P, Zhang T, Zhu X, Zhang M, Chen M, Du P, Wang GW, Ji H, Yang J, Yang S (2019) Angew Chem Int Ed 58:1479–1483. https://doi.org/10.1002/anie.201813218
Daukiya L, Teyssandier J, Eyley S, El Kazzi S, Rodriguez G, Miriam C, Pradhan B, Thielemans W, Hofkens J, De Feyter S (2021) Nanoscale 13:2972–2981. https://doi.org/10.1039/d0nr07310e
Chu XS, Yousaf A, Li DO, Tang AA, Debnath A, Ma D, Green AA, Santos EJG, Wang QH (2018) Chem Mater 30:2112–2118. https://doi.org/10.1021/acs.chemmater.8b00173
Yan EX, Caban-Acevedo M, Papadantonakis KM, Brunschwig BS, Lewis NS (2020) ACS Mater Lett 2:133–139. https://doi.org/10.1021/acsmaterialslett.9b00241
Knirsch KC, Berner NC, Nerl HC, Cucinotta CS, Gholamvand Z, McEvoy N, Wang Z, Abramovic I, Vecera P, Halik M, Sanvito S, Duesberg GS, Nicolosi V, Hauke F, Hirsch A, Coleman JN, Backes C (2015) ACS Nano 9:6018–6030. https://doi.org/10.1021/acsnano.5b00965
Casademont H, Fillaud L, Lefevre X, Jousselme B, Derycke V (2016) J Phys Chem C 120:9506–9510. https://doi.org/10.1021/acs.jpcc.6b01630
Er E, Hou HL, Criado A, Langer J, Möller M, Erk N, Liz-Marzán LM, Prato M (2019) Chem Mater 31:5725–5734. https://doi.org/10.1021/acs.chemmater.9b01698
Park Y, Shin S, An Y, Ahn JG, Shin G, Ahn C, Bang J, Baik J, Kim Y, Jung J, Lim H (2020) ACS Appl Mater Interfaces 12:40870–40878. https://doi.org/10.1021/acsami.0c09096
Xin C, Cian B, Lloret V, Badylan NM, Wolff S, Gillen R, Stimpel-Lindner T, Maultzsch J, Duesberg G, Knirsch K, Hirsch A (2021) Angew Chem Int Ed 60:13484–13492. https://doi.org/10.1002/anie.202103353
Li DO, Chu XS, Wang QH (2019) Langmuir 35:5693–5701. https://doi.org/10.1021/acs.langmuir.8b04288
Lihter M, Graf M, Iveković D, Zhang M, Shen TH, Zhao Y, Macha M, Tileli V, Radenovic A (2021) ACS Appl Nano Mater 4:1076–1084. https://doi.org/10.1021/acsanm.0c02628
Yu T, Mathias D, Lu S, Xu W, Naushad M, Szunerits S, Boukherroub R (2020) Sep Purif Technol 238:116420. https://doi.org/10.1016/j.seppur.2019.116420
Jiang P, Zhang B, Liu Z, Chen Y (2019) Nanoscale 11:20449–20455. https://doi.org/10.1039/c9nr06604g
Liu M, Zhu H, Wang Y, Sevencan C, Li BL (2021) ACS Mater Lett 3:462–496. https://doi.org/10.1021/acsmaterialslett.1c00073
Wang H, Zhang J, Wua Y, Huang H, Lia G, Zhang X, Wang Z (2016) Appl Surf Sci 384:287–293. https://doi.org/10.1016/j.apsusc.2016.05.060
Jing H, Yeo H, Lyu B, Ryou J, Choi S, Park JH, Lee BH, Kim YH, Lee S (2021) ACS Nano 15:1388–1396. https://doi.org/10.1021/acsnano.0c08664
Zhang P, Wang L, Huang Z, Yu J, Li Z, Deng H, Yin T, Yuan L, Gibson JK, Mei L, Zheng L, Wang H, Chai Z, Shi W (2020) ACS Appl Mater Interfaces 12:15579–15587. https://doi.org/10.1021/acsami.0c00861
Boota M, Urbankowski P, Porzio W, Barba L, Osti NC, Bleuel M, Keum JK, Mamontov E (2020) ACS Appl Energy Mater 3:4127–4133. https://doi.org/10.1021/acsaem.0c00314
Gomberg M, Bachmann WE (1924) J Am Chem Soc 42:2339–2343. https://doi.org/10.1039/c7cs00150a
Amaya T, Jin Y, Tobisu M (2019) Tetrahedron Lett 39:151062. https://doi.org/10.1016/j.tetlet.2019.151062
Berisha A, Combellas C, Kanoufi F, Pinson J, Podvorica FI, Ustaze S (2010) Chem Mater 22:2962–2969. https://doi.org/10.1021/cm100295n
Deniau G, Azoulay L, Bougerolles L, Palacin S (2006) Chem Mater 18:5421–5428. https://doi.org/10.1021/cm060739t
Tessier L, Deniau G, Charleux B, Palacin S (2009) Chem Mater 21:4261–4274. https://doi.org/10.1021/cm901430t
Hetemi D, Kanoufi F, Combellas C, Pinson J, Podvorica FI (2014) Langmuir 30:13907–13913. https://doi.org/10.1021/la503833j
Lund H, Daasbjerg K, Lund T, Occhialini D, Pedersen SU (1997) Acta Chem Scandinavica 51:135–144. https://doi.org/10.3891/acta.chem.scand.51-0135
Koefoed L, Pedersen SU, Daasbjerg K (2017) Covalent modification of glassy carbon surfaces by electrochemical grafting of aryl iodides. Langmuir 33:3217–3222. https://doi.org/10.1021/acs.langmuir.7b00300
Jouikov V, Simonet J (2012) Electrochem Commun 15:93–96. https://doi.org/10.1016/j.elecom.2011.12.008
Huang Y-F, Wu DY, Wang A, Ren B, Rondinini S, Tian Z-Q, Amatore C (2010) J Am Chem Soc 132:17199–17210. https://doi.org/10.1021/ja106049c
Hetemi D, Medard J, Decorse P, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2016) Langmuir 32:6335–6342. https://doi.org/10.1021/acs.langmuir.6b01557
Hetemi D, Combellas C, Kanoufi F, Podvorica FI (2021) ChemPhysChem 22:1–7. https://doi.org/10.1002/cphc.202100296
Pause L, Robert M, Saveant J-M (1999) J Am Chem Soc 121:7158–7159. https://doi.org/10.1021/ja991365q
Combellas C, Kanoufi F, Pinson J, Podvorica FI (2019) Elec Com 98:119–123. https://doi.org/10.1016/j.elecom.2018.12.005
Savéant J-M, Bethel D (eds) (1990) Advances in physical organic chemistry, vol 26. Academic Press, p 39. https://doi.org/10.1016/S0065-3160(08)60044-1
Smida H, Lebegue E, Bergamini JF, Barriere F, Lagrost C (2018) Bioelectrochemistry 120:157–165. https://doi.org/10.1016/j.bioelechem.2017.12.006
Hetemi D, Hazimeh H, Decorse P, Galtayries A, Combellas C, Kanoufi F, Pinson J, Podvorica FI (2015) Langmuir 31:5046–5415. https://doi.org/10.1021/acs.langmuir.5b00754
Medard J, Berisha A, Decorse P, Kanoufi F, Combellas C, Pinson J, Podvorica FI (2020) Elec Acta 345:136170. https://doi.org/10.1016/j.electacta.2020.136170
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Pinson, J., Podvorica, F. (2022). Principle, General Features and Scope of the Reaction, Recent Advances, Future Prospects. In: Chehimi, M.M., Pinson, J., Mousli, F. (eds) Aryl Diazonium Salts and Related Compounds. Physical Chemistry in Action. Springer, Cham. https://doi.org/10.1007/978-3-031-04398-7_1
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