{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T06:58:38Z","timestamp":1791097118767,"version":"4.1.0"},"reference-count":65,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2013,12,11]],"date-time":"2013-12-11T00:00:00Z","timestamp":1386720000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2014,1,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Self\u2010assembly of a series of carboxylic acid\u2010functionalized naphthalene diimide (NDI) chromophores with a varying number (<jats:italic>n<\/jats:italic>=1\u20134) of methylene spacers between the NDI ring and the carboxylic acid group has been studied. The derivatives show pronounced aggregation due to the synergistic effects of H\u2010bonding between the carboxylic acid groups in a <jats:italic>syn<\/jats:italic>\u2013<jats:italic>syn<\/jats:italic> catemer motif and \u03c0\u2005stacking between the NDI chromophores. Solvent\u2010dependent UV\/Vis studies reveal the existence of monomeric dye molecules in a \u201cgood\u201d solvent such as chloroform and self\u2010assembly in \u201cbad\u201d solvents such as methylcyclohexane. The propensity of self\u2010assembly is comparable for all samples. Temperature\u2010dependent spectroscopic studies show high thermal stability of the H\u2010bonding\u2010mediated self\u2010assembled structures. In the presence of a protic solvent such as MeOH, self\u2010assembly can be suppressed, suggesting a decisive role of H\u2010bonding, whereas \u03c0\u2005stacking is more a consequence of than a cause for self\u2010assembly. <jats:italic>Syn<\/jats:italic>\u2013<jats:italic>syn<\/jats:italic> catemer\u2010type H\u2010bonding is supported by powder XRD studies and the results corroborate well with DFT calculations. The morphology as determined by AFM is found to be dependent on the value of <jats:italic>n<\/jats:italic>; with increasing <jats:italic>n<\/jats:italic>, the morphology gradually shifts from 2D nanosheets to 1D nanofibers. Emission spectra show sharp emission bands with relatively small Stokes shifts. In addition, a rather broad emission band is observed at longer wavelengths because of the in situ formation of excimer\u2010type species. Due to such a heterogeneous nature, the emission spectrum spans almost the entire red\u2013green\u2013blue region. Depending on the value of <jats:italic>n<\/jats:italic>, the ratio of intensities of the two emission bands is changed, which results in a tunable luminescent color. Furthermore, in the case of <jats:italic>n<\/jats:italic>=1 and 3, almost pure white light emission is observed. Time\u2010resolved photoluminescence spectra show a very short lifetime (a few picoseconds) of monomeric dye molecules and biexponential decays with longer lifetimes (on the order of nanoseconds) for aggregated species. Current\u2013voltage measurements show electrical conductivity in the range of 10<jats:sup>\u22124<\/jats:sup>\u2005S\u2009cm<jats:sup>\u22121<\/jats:sup> for the aggregated chromophores, which is four orders of magnitude higher than the value for a structurally similar NDI control molecule lacking the H\u2010bonding functionality.<\/jats:p>","DOI":"10.1002\/chem.201303379","type":"journal-article","created":{"date-parts":[[2013,12,11]],"date-time":"2013-12-11T08:52:36Z","timestamp":1386751956000},"page":"760-771","source":"Crossref","is-referenced-by-count":110,"title":["Self\u2010Assembly of Carboxylic Acid Appended Naphthalene Diimide Derivatives with Tunable Luminescent Color and Electrical Conductivity"],"prefix":"10.1002","volume":"20","author":[{"given":"Mijanur Rahaman","family":"Molla","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dominik","family":"Gehrig","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lisa","family":"Roy","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Valentin","family":"Kamm","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ankan","family":"Paul","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fr\u00e9d\u00e9ric","family":"Laquai","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Suhrit","family":"Ghosh","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2013,12,11]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm101817h"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochemrev.2006.11.001"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar3002969"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2nr32140h"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar7000364"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1039\/B917751E"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1039\/B611422A"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc14990c"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200503158"},{"key":"e_1_2_6_10_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503158"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/jz101219y"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm102772x"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15031F"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106767"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201002307"},{"key":"e_1_2_6_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201002307"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800915"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103600"},{"key":"e_1_2_6_18_2","first-page":"8","volume":"8","author":"Moorthy J. N.","year":"2008","journal-title":"J. Ind. Inst. Sci."},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017637i"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.200600046"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200601500"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja807996y"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja106807u"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.368"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp106177n"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.201204407"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2jm35012b"},{"key":"e_1_2_6_28_2","unstructured":"For supramolecular assemblies of various NDI\u2010linked systems see:"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc00078g"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/B615857A"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/B906115K"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja051260p"},{"key":"e_1_2_6_33_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.657"},{"key":"e_1_2_6_34_2","doi-asserted-by":"crossref","first-page":"5459","DOI":"10.1002\/ange.201000807","volume":"122","author":"Au\u2010Yeung H. Y.","year":"2010","journal-title":"Angew. Chem."},{"key":"e_1_2_6_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000807"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0809934106"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906634h"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1038\/375303a0"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja061649s"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200400651"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1007\/128_2011_305"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1ob06147j"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201305356"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201003415"},{"key":"e_1_2_6_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201003415"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja205868b"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201300039"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701139"},{"key":"e_1_2_6_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701139"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1nr10151j"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ct900541n"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1107\/S0365110X58001341"},{"key":"e_1_2_6_50_2","doi-asserted-by":"crossref","unstructured":"Spickermann C. \u201cEntropies of Condensed Phases and Complex Systems\u201d Springer These Berlin 2010 chap. 3 pp.\u200576\u201380 and references therein.","DOI":"10.1007\/978-3-642-15736-3"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1039\/C2CC36536G"},{"key":"e_1_2_6_52_2","unstructured":"Discontinuous sheetlike morphology is also observed occasionally in AFM."},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm102343r"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochem.2005.04.038"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0612269"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.synthmet.2009.04.003"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1068195"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/adfm.201101001"},{"key":"e_1_2_6_59_2","volume-title":"Purification of Laboratory Chemicals","author":"Perrin D. D.","year":"1980"},{"key":"e_1_2_6_60_2","unstructured":"Please see ref.\u2005[3] in the Supporting Information."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201303379","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201303379","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T16:15:53Z","timestamp":1760285753000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201303379"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2013,12,11]]},"references-count":65,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2014,1,13]]}},"alternative-id":["10.1002\/chem.201303379"],"URL":"https:\/\/doi.org\/10.1002\/chem.201303379","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2013,12,11]]}}}