Barbituric Derivative Nanoaggregates with Aggregation-Induced Emission and Mechanofluorochromism

<div>(a) FL spectra of TTB, TTTB, and TOB in THF/H<sub>2</sub>O with different water fractions (<span class="nowrap"><svg height="12.7178pt" id="M41" style="vertical-align:-3.42947pt" version="1.1" viewbox="-0.0498162 -9.28833 13.6008 12.7178" width="13.6008pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M619 670C619 686 593 712 555 712S459 686 410 634S335 504 320 430H250L219 400L222 388H312L258 73C223 -133 201 -166 187 -180C175 -191 158 -199 140 -199C123 -199 88 -188 74 -172C68 -166 63 -164 54 -171C38 -185 23 -201 23 -215C23 -236 60 -261 93 -261C122 -261 161 -247 207 -200C268 -138 300 -71 337 94C365 220 376 277 394 387L501 399L521 430H401C432 623 464 665 501 665C524 665 544 651 567 627C577 617 583 618 592 625C601 631 619 651 619 670Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,6.721,3.132)"><path d="M696 437H516V411C580 402 587 397 574 345C555 271 527 183 505 114H503C461 222 420 328 383 432H357C315 316 278 214 241 118H239C214 195 189 274 165 350C151 396 156 402 216 411V437H9V411C57 405 65 398 83 346C125 226 162 108 199 -11H227C267 100 308 199 346 300C387 195 428 97 468 -11H497C542 124 587 257 617 337C637 392 646 404 696 411V437Z"></path></g></svg>).</span> (b) FL peak location (blue) and emission intensity (red) of TTB, TTTB, and TOB versus <svg height="12.7178pt" id="M42" style="vertical-align:-3.42947pt" version="1.1" viewbox="-0.0498162 -9.28833 13.6008 12.7178" width="13.6008pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M619 670C619 686 593 712 555 712S459 686 410 634S335 504 320 430H250L219 400L222 388H312L258 73C223 -133 201 -166 187 -180C175 -191 158 -199 140 -199C123 -199 88 -188 74 -172C68 -166 63 -164 54 -171C38 -185 23 -201 23 -215C23 -236 60 -261 93 -261C122 -261 161 -247 207 -200C268 -138 300 -71 337 94C365 220 376 277 394 387L501 399L521 430H401C432 623 464 665 501 665C524 665 544 651 567 627C577 617 583 618 592 625C601 631 619 651 619 670Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,6.721,3.132)"><path d="M696 437H516V411C580 402 587 397 574 345C555 271 527 183 505 114H503C461 222 420 328 383 432H357C315 316 278 214 241 118H239C214 195 189 274 165 350C151 396 156 402 216 411V437H9V411C57 405 65 398 83 346C125 226 162 108 199 -11H227C267 100 308 199 346 300C387 195 428 97 468 -11H497C542 124 587 257 617 337C637 392 646 404 696 411V437Z"></path></g></svg> in THF/H<sub>2</sub>O (concentration: <span class="nowrap"><svg height="13.5868pt" id="M43" style="vertical-align:-2.1507pt" version="1.1" viewbox="-0.0498162 -11.4361 87.1974 13.5868" width="87.1974pt" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink"><g transform="matrix(.013,0,0,-0.013,0,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g><g transform="matrix(.013,0,0,-0.013,6.24,0)"><path d="M113 -12C146 -12 170 11 170 46C170 78 146 103 114 103S58 78 58 46C58 11 82 -12 113 -12Z"></path></g><g transform="matrix(.013,0,0,-0.013,9.204,0)"><path d="M241 635C89 635 35 457 35 312C35 153 89 -12 240 -12C390 -12 443 166 443 312C443 466 390 635 241 635ZM238 602C329 602 354 454 354 312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g><g transform="matrix(.013,0,0,-0.013,18.35,0)"><path d="M528 54L331 254L528 455L492 493L294 291L96 493L60 455L257 254L60 54L96 16L294 217L492 16L528 54Z"></path></g><g transform="matrix(.013,0,0,-0.013,28.886,0)"><path d="M384 0V27C293 34 287 42 287 114V635C232 613 172 594 109 583V559L157 557C201 555 205 550 205 499V114C205 42 199 34 109 27V0H384Z"></path></g><g transform="matrix(.013,0,0,-0.013,35.126,0)"><path d="M241 635C89 635 35 457 35 312C35 153 89 -12 240 -12C390 -12 443 166 443 312C443 466 390 635 241 635ZM238 602C329 602 354 454 354 312C354 172 330 22 240 22C152 22 124 173 124 313S148 602 238 602Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,41.413,-5.741)"><path d="M556 236V289H56V236H556Z"></path></g><g transform="matrix(.0091,0,0,-0.0091,46.973,-5.741)"><path d="M158 548H390L417 615L410 623H122L83 318C105 326 143 337 185 337C296 337 350 275 350 188C350 116 308 42 225 42C164 42 122 74 100 93C90 101 82 99 72 92C60 82 51 68 50 59C48 46 52 38 66 24C82 9 125 -12 172 -12C225 -11 292 15 346 59C408 108 437 166 437 226C437 309 371 397 242 397C214 397 170 382 133 369L158 548Z"></path></g><g transform="matrix(.013,0,0,-0.013,54.115,0)"><path d="M797 0V26C739 32 732 36 732 103V296C732 394 682 449 605 449C576 449 550 437 529 423C504 407 475 389 446 366C425 418 382 449 334 449C303 449 279 437 253 421C222 403 201 385 180 371V452C135 432 85 419 41 411V388C99 379 102 374 102 310V103C102 38 93 32 27 26V0H238V26C189 32 180 38 180 103V338C210 363 250 390 289 390C351 390 377 348 377 275V103C377 37 368 32 306 26V0H520V26C465 32 456 38 456 101V296C456 314 455 326 453 338C491 369 529 390 565 390C628 390 653 345 653 274V107C653 36 642 32 583 26V0H797Z"></path></g><g transform="matrix(.013,0,0,-0.013,64.71,0)"><path d="M257 449C165 449 37 374 37 209C37 98 119 -12 256 -12C355 -12 473 65 473 226C473 349 381 449 257 449ZM244 416C333 416 380 320 380 204C380 67 329 21 267 21C184 21 130 115 130 241C130 354 184 416 244 416Z"></path></g><g transform="matrix(.013,0,0,-0.013,71.249,0)"><path d="M238 0V26C174 32 166 38 166 104V712C132 700 70 683 18 677V653C81 647 87 645 87 577V104C87 38 78 32 15 26V0H238Z"></path></g><g transform="matrix(.013,0,0,-0.013,74.615,0)"><path d="M368 703H309L44 -163H104L368 703Z"></path></g><g transform="matrix(.013,0,0,-0.013,79.976,0)"><path d="M495 163C480 117 462 85 444 65C421 39 387 34 332 34C290 34 256 36 236 47C218 57 213 77 213 131V526C213 612 222 616 301 622V650H40V622C122 616 128 611 128 526V126C128 41 120 34 36 28V0H489C498 31 519 126 525 157L495 163Z"></path></g></svg>;</span> excitation wavelength, TTB: 360 nm, TTTB: 480 nm, and TOB: 360 nm).</div>

Journal of Nanomaterials

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Figure 2

Figure 2: Barbituric Derivative Nanoaggregates with Aggregation-Induced Emission and Mechanofluorochromism 